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


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof. Wei Zhang'
_publ_contact_author_email       zhangwei6275@lzu.edu.cn

_publ_section_title              
;
Photoinduced chlorine atom-transfer
cyclization/photohydrolysis of 3-acyl-2-chloro-N-(o-phenylalkynyl)pyrroles:
a one-pot synthesis of benzoyl-substituted fused pyrroles
;
loop_
_publ_author_name
'Wei Zhang'
'Shen Lu'

# Attachment 'P21n.cif'

data_p21n
_database_code_depnum_ccdc_archive 'CCDC 807627'
#TrackingRef 'P21n.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cl2 N O3'
_chemical_formula_weight         336.16

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   6.393(13)
_cell_length_b                   9.37(2)
_cell_length_c                   26.44(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.38(2)
_cell_angle_gamma                90.00
_cell_volume                     1582(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    492
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      15.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8985
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7140
_diffrn_reflns_av_R_equivalents  0.1683
_diffrn_reflns_av_sigmaI/netI    0.2477
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2793
_reflns_number_gt                798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0746P)^2^+0.0000P] 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_number_reflns         2793
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3128
_refine_ls_R_factor_gt           0.1024
_refine_ls_wR_factor_ref         0.2454
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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
C1 C 0.9524(14) 0.0667(11) 0.1114(4) 0.077(3) Uani 1 1 d . . .
C2 C 0.7730(15) 0.1362(11) 0.0965(3) 0.079(3) Uani 1 1 d . . .
C3 C 0.6895(14) 0.2032(10) 0.1393(3) 0.065(3) Uani 1 1 d . . .
C4 C 0.8249(14) 0.1644(9) 0.1799(3) 0.056(2) Uani 1 1 d . . .
C5 C 0.8527(12) 0.1872(9) 0.2351(3) 0.056(2) Uani 1 1 d . . .
H5 H 0.8458 0.2895 0.2426 0.068 Uiso 1 1 calc R . .
C6 C 1.0832(12) 0.1310(10) 0.2461(3) 0.075(3) Uani 1 1 d . . .
H6A H 1.1816 0.2099 0.2480 0.090 Uiso 1 1 calc R . .
H6B H 1.0929 0.0787 0.2778 0.090 Uiso 1 1 calc R . .
C7 C 1.1291(13) 0.0326(10) 0.2015(3) 0.077(3) Uani 1 1 d . . .
H7A H 1.2722 0.0431 0.1912 0.093 Uiso 1 1 calc R . .
H7B H 1.1032 -0.0667 0.2096 0.093 Uiso 1 1 calc R . .
C8 C 0.6969(13) 0.1069(10) 0.2663(4) 0.057(2) Uani 1 1 d . . .
C9 C 0.6891(13) 0.1306(9) 0.3215(3) 0.059(2) Uani 1 1 d . . .
C10 C 0.8244(13) 0.2228(10) 0.3482(4) 0.075(3) Uani 1 1 d . . .
H10 H 0.9166 0.2783 0.3303 0.090 Uiso 1 1 calc R . .
C11 C 0.8265(15) 0.2349(11) 0.4005(4) 0.094(3) Uani 1 1 d . . .
H11 H 0.9218 0.2939 0.4178 0.112 Uiso 1 1 calc R . .
C12 C 0.6836(18) 0.1569(13) 0.4255(3) 0.098(4) Uani 1 1 d . . .
C13 C 0.5404(15) 0.0680(12) 0.4016(4) 0.095(4) Uani 1 1 d . . .
H13 H 0.4418 0.0191 0.4198 0.114 Uiso 1 1 calc R . .
C14 C 0.5468(14) 0.0532(9) 0.3495(4) 0.077(3) Uani 1 1 d . . .
H14 H 0.4547 -0.0095 0.3328 0.092 Uiso 1 1 calc R . .
C15 C 1.0973(18) -0.0162(13) 0.0817(4) 0.108(4) Uani 1 1 d . . .
H15 H 1.0673 -0.0237 0.0471 0.129 Uiso 1 1 calc R . .
C16 C 0.5033(15) 0.2892(11) 0.1422(4) 0.085(3) Uani 1 1 d . . .
H16 H 0.4290 0.3081 0.1120 0.101 Uiso 1 1 calc R . .
Cl1 Cl 0.6651(4) 0.1461(4) 0.03613(10) 0.1262(13) Uani 1 1 d . . .
Cl2 Cl 0.6745(6) 0.1752(4) 0.49136(11) 0.1656(17) Uani 1 1 d . . .
N1 N 0.9799(11) 0.0847(8) 0.1624(3) 0.064(2) Uani 1 1 d . . .
O1 O 0.5773(9) 0.0210(6) 0.2444(2) 0.0673(18) Uani 1 1 d . . .
O2 O 0.4343(10) 0.3394(7) 0.1805(3) 0.096(2) Uani 1 1 d . . .
O3 O 1.2529(12) -0.0757(9) 0.0985(3) 0.134(3) 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
C1 0.047(7) 0.116(10) 0.067(8) -0.004(6) 0.000(6) 0.027(6)
C2 0.067(7) 0.098(8) 0.071(7) 0.001(6) -0.001(6) 0.019(6)
C3 0.053(6) 0.087(8) 0.055(6) 0.001(6) -0.001(5) 0.017(6)
C4 0.049(6) 0.059(7) 0.061(7) -0.010(5) 0.012(5) -0.009(5)
C5 0.049(6) 0.045(6) 0.075(6) 0.003(5) 0.005(5) 0.000(5)
C6 0.050(6) 0.099(8) 0.075(7) 0.009(6) 0.001(5) -0.015(6)
C7 0.053(6) 0.089(8) 0.090(8) 0.013(7) -0.014(6) 0.008(6)
C8 0.044(6) 0.045(7) 0.082(7) -0.004(6) -0.003(5) 0.015(5)
C9 0.055(6) 0.046(7) 0.074(7) -0.004(5) -0.002(5) -0.009(5)
C10 0.069(7) 0.076(8) 0.080(7) -0.004(6) 0.000(6) -0.032(6)
C11 0.085(8) 0.114(9) 0.083(8) -0.016(7) 0.018(7) -0.048(7)
C12 0.100(9) 0.134(10) 0.059(7) -0.017(7) 0.004(6) -0.043(8)
C13 0.078(8) 0.131(11) 0.075(8) -0.005(7) 0.010(6) -0.033(7)
C14 0.070(7) 0.065(7) 0.096(8) -0.005(6) 0.011(6) -0.019(5)
C15 0.088(9) 0.151(12) 0.083(8) -0.021(8) 0.005(7) 0.032(8)
C16 0.064(8) 0.098(10) 0.091(8) 0.010(7) -0.011(6) 0.020(7)
Cl1 0.106(2) 0.206(3) 0.0652(18) -0.005(2) -0.0098(15) 0.045(2)
Cl2 0.189(3) 0.237(4) 0.071(2) -0.016(2) 0.010(2) -0.096(3)
N1 0.046(5) 0.083(6) 0.063(6) -0.001(5) 0.000(4) 0.004(4)
O1 0.060(4) 0.062(5) 0.078(4) 0.001(4) -0.013(3) 0.000(3)
O2 0.080(5) 0.094(6) 0.116(6) 0.001(5) 0.019(4) 0.029(4)
O3 0.092(6) 0.182(9) 0.126(7) -0.022(6) -0.005(5) 0.070(6)

_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
C1 C2 1.362(10) . ?
C1 N1 1.363(10) . ?
C1 C15 1.463(12) . ?
C2 C3 1.417(11) . ?
C2 Cl1 1.716(10) . ?
C3 C4 1.400(11) . ?
C3 C16 1.442(11) . ?
C4 N1 1.339(9) . ?
C4 C5 1.477(11) . ?
C5 C8 1.520(10) . ?
C5 C6 1.581(10) . ?
C5 H5 0.9800 . ?
C6 C7 1.536(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.460(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.237(9) . ?
C8 C9 1.479(11) . ?
C9 C10 1.394(10) . ?
C9 C14 1.398(10) . ?
C10 C11 1.385(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(12) . ?
C12 Cl2 1.754(10) . ?
C13 C14 1.386(12) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O3 1.208(11) . ?
C15 H15 0.9300 . ?
C16 O2 1.216(10) . ?
C16 H16 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
C2 C1 N1 107.4(8) . . ?
C2 C1 C15 130.0(10) . . ?
N1 C1 C15 122.6(9) . . ?
C1 C2 C3 108.8(8) . . ?
C1 C2 Cl1 126.6(8) . . ?
C3 C2 Cl1 124.6(8) . . ?
C4 C3 C2 104.8(8) . . ?
C4 C3 C16 126.1(9) . . ?
C2 C3 C16 129.1(10) . . ?
N1 C4 C3 108.8(8) . . ?
N1 C4 C5 111.2(8) . . ?
C3 C4 C5 140.0(9) . . ?
C4 C5 C8 114.2(7) . . ?
C4 C5 C6 101.9(7) . . ?
C8 C5 C6 111.2(7) . . ?
C4 C5 H5 109.7 . . ?
C8 C5 H5 109.7 . . ?
C6 C5 H5 109.7 . . ?
C7 C6 C5 105.3(7) . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6A 110.7 . . ?
C7 C6 H6B 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
N1 C7 C6 101.7(7) . . ?
N1 C7 H7A 111.4 . . ?
C6 C7 H7A 111.4 . . ?
N1 C7 H7B 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
O1 C8 C9 120.9(8) . . ?
O1 C8 C5 118.3(9) . . ?
C9 C8 C5 120.8(8) . . ?
C10 C9 C14 117.2(9) . . ?
C10 C9 C8 123.1(9) . . ?
C14 C9 C8 119.6(9) . . ?
C11 C10 C9 122.4(9) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C12 C11 C10 117.5(9) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 C13 123.3(10) . . ?
C11 C12 Cl2 118.7(9) . . ?
C13 C12 Cl2 117.9(9) . . ?
C12 C13 C14 118.1(9) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C13 C14 C9 121.4(9) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
O3 C15 C1 125.4(10) . . ?
O3 C15 H15 117.3 . . ?
C1 C15 H15 117.3 . . ?
O2 C16 C3 126.2(10) . . ?
O2 C16 H16 116.9 . . ?
C3 C16 H16 116.9 . . ?
C4 N1 C1 110.1(8) . . ?
C4 N1 C7 114.4(8) . . ?
C1 N1 C7 135.4(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.8(11) . . . . ?
C15 C1 C2 C3 -179.0(10) . . . . ?
N1 C1 C2 Cl1 -179.5(7) . . . . ?
C15 C1 C2 Cl1 -0.4(17) . . . . ?
C1 C2 C3 C4 -2.3(11) . . . . ?
Cl1 C2 C3 C4 179.0(7) . . . . ?
C1 C2 C3 C16 179.6(9) . . . . ?
Cl1 C2 C3 C16 0.9(15) . . . . ?
C2 C3 C4 N1 1.9(10) . . . . ?
C16 C3 C4 N1 -179.9(8) . . . . ?
C2 C3 C4 C5 179.5(10) . . . . ?
C16 C3 C4 C5 -2.3(17) . . . . ?
N1 C4 C5 C8 -108.8(8) . . . . ?
C3 C4 C5 C8 73.6(13) . . . . ?
N1 C4 C5 C6 11.2(9) . . . . ?
C3 C4 C5 C6 -166.4(10) . . . . ?
C4 C5 C6 C7 -20.9(8) . . . . ?
C8 C5 C6 C7 101.3(8) . . . . ?
C5 C6 C7 N1 22.6(8) . . . . ?
C4 C5 C8 O1 6.9(11) . . . . ?
C6 C5 C8 O1 -107.8(9) . . . . ?
C4 C5 C8 C9 -173.3(8) . . . . ?
C6 C5 C8 C9 71.9(9) . . . . ?
O1 C8 C9 C10 178.0(8) . . . . ?
C5 C8 C9 C10 -1.8(12) . . . . ?
O1 C8 C9 C14 1.0(12) . . . . ?
C5 C8 C9 C14 -178.8(7) . . . . ?
C14 C9 C10 C11 2.6(14) . . . . ?
C8 C9 C10 C11 -174.5(9) . . . . ?
C9 C10 C11 C12 -2.8(15) . . . . ?
C10 C11 C12 C13 0.2(17) . . . . ?
C10 C11 C12 Cl2 -177.4(8) . . . . ?
C11 C12 C13 C14 2.4(17) . . . . ?
Cl2 C12 C13 C14 180.0(8) . . . . ?
C12 C13 C14 C9 -2.5(15) . . . . ?
C10 C9 C14 C13 0.2(13) . . . . ?
C8 C9 C14 C13 177.4(8) . . . . ?
C2 C1 C15 O3 -179.2(12) . . . . ?
N1 C1 C15 O3 -0.2(18) . . . . ?
C4 C3 C16 O2 -1.1(16) . . . . ?
C2 C3 C16 O2 176.7(10) . . . . ?
C3 C4 N1 C1 -0.8(10) . . . . ?
C5 C4 N1 C1 -179.2(7) . . . . ?
C3 C4 N1 C7 -177.9(7) . . . . ?
C5 C4 N1 C7 3.7(10) . . . . ?
C2 C1 N1 C4 -0.6(10) . . . . ?
C15 C1 N1 C4 -179.8(9) . . . . ?
C2 C1 N1 C7 175.6(9) . . . . ?
C15 C1 N1 C7 -3.6(16) . . . . ?
C6 C7 N1 C4 -17.1(9) . . . . ?
C6 C7 N1 C1 166.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051