# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001
# CCDC Number: 188/286

data_CRYSTALS_cif
#  Paper title: N-(3-cyano-2-propynyl)carbazole: Synthesis, Crystal Structure
#   and Solid-Sttae Reactivity by U. Drechsler, D. J. Sandman and
#   B. M. Foxman (Manuscript mailed to Perkin 2: 11 Sept 2000)
_audit_creation_date        00-06-09
_audit_creation_method CRYSTALS_ver_07-07-97
#  N-(3-cyano-2-propynyl)carbazole (Compound 1)
#****************************************************************************
_publ_section_references # 
;
Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,
Polidori, G.  & Camalli, M. (1994) SIR92 - a program for automatic solution of
crystal structures by direct methods. J. Appl. Cryst. (27), 435
 
Carruthers, J.R. and Watkin, D.J. (1979), (Chebychev Weighting)
Acta Cryst, A35, 698-699
 
Fair, C. K. (1990). MolEN, An Interactive Structure Solution Procedure, 
Enraf-Nonius, Delft, The Netherlands.

North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), (Psi
correction), Acta Cryst, A24, 351-359
 
Sheldrick, G.M. (1986).  SHELXS86. Program for the solution of
crystal structures.  Univ. of Gottingen, Federal Republic of Germany.

Straver, L. H. (1992). CAD4-EXPRESS, Enraf-Nonius, Delft, The Netherlands.
 
Watkin, D.J., Prout, C.K. Carruthers, R.J. & Betteridge, P.W. (1996) CRYSTALS
Issue 10. Chemical Crystallography Laboratory, OXFORD, UK.
 
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.
 
Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical
Crystallography Laboratory, Oxford, UK.
;
_publ_section_figure_captions  #Captions to figures
;
?
;
_publ_section_acknowledgements
;
 ?
;
#==========================================================================
# Now, all the strucure specific goodies
#==========================================================================
_computing_data_collection 'CAD4-EXPRESS (Straver, 1992)'
_computing_cell_refinement 'CAD4-EXPRESS (Straver, 1992)'
_computing_data_reduction
;
MolEN (Fair, C. K., 1990)
;
_computing_structure_refinement
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_publication_material
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_molecular_graphics
;
 CAMERON (Watkin, Prout & Pearce,  1996)
;
# _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)'
 
#==========================================================================
# General computing
#==========================================================================
_computing_structure_refinement
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_publication_material
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_molecular_graphics
;
 CAMERON (Watkin, Prout & Pearce,  1996)
;
# choose one of the following two lines
# _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)'
 
#==========================================================================
#==========================================================================
# Diffractometer details
#==========================================================================
_diffrn_radiation_monochromator      graphite
_diffrn_measurement_device_type     '  Enraf-nonius CAD4 '
_computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)'
#==========================================================================
# General computing
#==========================================================================
_computing_structure_refinement
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_publication_material
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_molecular_graphics
;
 CAMERON (Watkin, Prout & Pearce,  1996)
;
# choose one of the following two lines
# _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)'
_computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)'
 
#==========================================================================
 
_chemical_name_systematic       N-(3-cyano-2-propynyl)carbazole
;
?
;
_chemical_melting_point                    'not measured'
# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse'
_refine_ls_matrix_type                      full
# choose from 'heavy, direct, difmap, geom'
_atom_sites_solution_primary                direct
# _atom_sites_solution_secondary            difmap
_atom_sites_solution_hydrogens              geom
# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed'
_refine_ls_hydrogen_treatment               noref
#****************************************************************************
_cell_length_a 6.5553(6)
_cell_angle_alpha 90.
_cell_length_b 11.388(3)
_cell_angle_beta  90.
_cell_length_c 16.275(3)
_cell_angle_gamma 90.
_cell_volume   1215.0
_symmetry_cell_setting 'Orthorhombic '
_symmetry_space_group_name_H-M 'P 21 21 21 '
loop_
 _symmetry_equiv_pos_as_xyz
 'x,y,z'
 'x+1/2,-y+1/2,-z'
 '-x,y+1/2,-z+1/2'
 '-x+1/2,-y,z+1/2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
 'N   '    0.0290    0.0180   12.2126    0.0057
    3.1322    9.8933    2.0125   28.9975    1.1663    0.5826  -11.5290
'International_Tables_Vol_IV_Table_2.2B'
 'C   '    0.0170    0.0090    2.3100   20.8439
    1.0200   10.2075    1.5886    0.5687    0.8650   51.6512    0.2156
'International_Tables_Vol_IV_Table_2.2B'
 'H   '    0.0000    0.0000    0.4930   10.5109
    0.3229   26.1257    0.1402    3.1424    0.0408   57.7997    0.0030
'International_Tables_Vol_IV_Table_2.2B'
_chemical_formula_sum
' C16 H10 N2 '
_chemical_formula_moiety
' C16 H10 N2 '
_chemical_compound_source
;
?
;
_chemical_formula_weight   230.27
_cell_measurement_reflns_used       25
_cell_measurement_theta_min       40
_cell_measurement_theta_max       46
_cell_measurement_temperature      294
_cell_formula_units_Z 4
_exptl_crystal_description ' needle '
_exptl_crystal_colour ' colorless '
_exptl_crystal_size_min 0.18
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_max 0.65
_exptl_crystal_density_diffrn 1.26
_exptl_crystal_density_meas 1.25(1)
_exptl_crystal_F_000 481.22
_exptl_absorpt_coefficient_mu 0.55
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details '\y scan,(North et al, 1968)'
_exptl_absorpt_correction_T_min 0.85
_exptl_absorpt_correction_T_max 0.90
# Sheldrick geometric definitions 0.89 0.90
_diffrn_standards_interval_time 7200 s
_diffrn_standards_interval_count 0
_diffrn_standards_number 3
_diffrn_standards_decay_% 0.00
_diffrn_ambient_temperature        294
_diffrn_reflns_number 1499
_reflns_number_total 1499
_diffrn_reflns_av_R_equivalents 0.00
# Number of reflections with Friedels Law is 1499
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1300
_diffrn_measured_fraction_theta_max 1.000
_reflns_number_observed 1300
_diffrn_reflns_theta_min 2.37
_diffrn_reflns_theta_max 78.00
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_limit_l_max 20
_reflns_limit_h_min 0
_reflns_limit_h_max 8
_reflns_limit_k_min 0
_reflns_limit_k_max 14
_reflns_limit_l_min 0
_reflns_limit_l_max 20
_reflns_observed_criterion  >1.96\s(I)
_refine_diff_density_min -0.12
_refine_diff_density_max 0.12
_refine_ls_number_reflns 1300
_refine_ls_number_parameters 164
_refine_ls_R_factor_obs 0.0353
_refine_ls_wR_factor_obs 0.0462
_refine_ls_goodness_of_fit_obs 1.0188
_refine_ls_shift/su_max 0.000374
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
 Chebychev polynomial with   3 parameters (Carruthers & Watkin, 1979)
 1.76 1.50 0.896
;
_diffrn_radiation_type       'Cu K\a'
_diffrn_radiation_wavelength      1.54178
_diffrn_measurement_method \w/2\q
 
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3
 
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_thermal_displace_type
N1 0.5391(3) 0.30207(13) 0.81950(11) 0.0708 1.0000 Uani
N2 0.3598(4) 0.75669(19) 0.96320(14) 0.0924 1.0000 Uani
C1 0.5587(3) 0.21855(15) 0.88143(12) 0.0622 1.0000 Uani
C2 0.3900(3) 0.14285(14) 0.87794(11) 0.0568 1.0000 Uani
C3 0.3771(4) 0.04939(16) 0.93233(13) 0.0689 1.0000 Uani
C4 0.5309(5) 0.03356(19) 0.98870(15) 0.0838 1.0000 Uani
C5 0.6947(5) 0.1103(2) 0.99203(17) 0.0892 1.0000 Uani
C6 0.7126(4) 0.20373(19) 0.93901(16) 0.0809 1.0000 Uani
C7 0.2613(3) 0.18450(16) 0.81232(11) 0.0606 1.0000 Uani
C8 0.0756(4) 0.1452(2) 0.77975(14) 0.0772 1.0000 Uani
C9 -0.0056(5) 0.2036(3) 0.71396(17) 0.1014 1.0000 Uani
C10 0.0901(6) 0.3003(3) 0.68042(15) 0.1061 1.0000 Uani
C11 0.2717(5) 0.3435(2) 0.71173(14) 0.0910 1.0000 Uani
C12 0.3575(4) 0.28347(16) 0.77831(12) 0.0674 1.0000 Uani
C13 0.6691(4) 0.40416(18) 0.80865(17) 0.0893 1.0000 Uani
C14 0.5931(4) 0.50630(16) 0.85371(15) 0.0736 1.0000 Uani
C15 0.5261(4) 0.58782(16) 0.88974(13) 0.0673 1.0000 Uani
C16 0.4384(4) 0.68072(17) 0.93022(13) 0.0683 1.0000 Uani
H31 0.2640 -0.0027 0.9307 0.0870 1.0000 Uiso
H41 0.5249 -0.0308 1.0258 0.1047 1.0000 Uiso
H51 0.7977 0.0980 1.0322 0.1145 1.0000 Uiso
H61 0.8255 0.2559 0.9417 0.1025 1.0000 Uiso
H81 0.0075 0.0794 0.8028 0.1004 1.0000 Uiso
H91 -0.1304 0.1770 0.6909 0.1312 1.0000 Uiso
H101 0.0297 0.3384 0.6345 0.1328 1.0000 Uiso
H111 0.3354 0.4110 0.6889 0.1140 1.0000 Uiso
H131 0.8022 0.3858 0.8279 0.1093 1.0000 Uiso
H132 0.6750 0.4230 0.7518 0.1093 1.0000 Uiso
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
N1 0.0799(11) 0.0449(7) 0.0877(11) 0.0048(7) 0.018(1) -0.0021(8)
N2 0.0880(13) 0.0718(11) 0.1175(15) -0.0206(12) 0.0088(13) -0.0006(11)
C1 0.0671(11) 0.0445(8) 0.075(1) -0.0071(7) 0.006(1) 0.0019(8)
C2 0.0675(11) 0.0423(7) 0.0606(9) -0.0068(6) 0.0029(9) 0.0033(8)
C3 0.0849(14) 0.0475(9) 0.0745(11) -0.0021(8) -0.0006(11) -0.005(1)
C4 0.1113(18) 0.056(1) 0.0847(13) 0.003(1) -0.0120(15) 0.0080(13)
C5 0.0991(17) 0.0700(12) 0.0985(15) -0.0094(12) -0.0312(15) 0.0158(14)
C6 0.0727(13) 0.0631(11) 0.1069(17) -0.0159(12) -0.0127(13) 0.0008(11)
C7 0.0709(11) 0.0513(8) 0.0597(8) -0.0097(7) 0.0056(9) 0.0069(9)
C8 0.0745(13) 0.0776(13) 0.0796(12) -0.0192(11) -0.0041(12) 0.0124(12)
C9 0.0984(19) 0.115(2) 0.0905(16) -0.0246(17) -0.0239(15) 0.0402(18)
C10 0.136(3) 0.112(2) 0.0698(13) -0.0071(14) -0.0143(16) 0.061(2)
C11 0.127(2) 0.0774(14) 0.0687(12) 0.0089(11) 0.0202(15) 0.0377(16)
C12 0.0864(14) 0.0541(9) 0.0618(9) -0.0022(8) 0.014(1) 0.015(1)
C13 0.0942(16) 0.052(1) 0.1218(18) -0.0031(11) 0.0425(15) -0.0075(12)
C14 0.0791(13) 0.0502(9) 0.0916(13) 0.0079(9) 0.0210(12) -0.0086(9)
C15 0.0715(11) 0.0489(9) 0.0816(12) 0.0034(9) 0.0067(11) -0.0057(9)
C16 0.0668(11) 0.055(1) 0.0831(12) -0.0014(9) -0.0005(11) -0.007(1)
_refine_ls_extinction_coef 39.0(47)
_refine_ls_extinction_method
    'Larson 1970 Crystallographic Computing eq 22'
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
N1 . C1 . 1.392(2)    yes
N1 . C12 . 1.383(3)    yes
N1 . C13 . 1.452(3)    yes
N2 . C16 . 1.141(3)    yes
C1 . C2 . 1.403(3)    yes
C1 . C6 . 1.387(3)    yes
C2 . C3 . 1.387(3)    yes
C2 . C7 . 1.441(3)    yes
C3 . C4 . 1.375(3)    yes
C4 . C5 . 1.386(4)    yes
C5 . C6 . 1.375(3)    yes
C7 . C8 . 1.402(3)    yes
C7 . C12 . 1.405(3)    yes
C8 . C9 . 1.368(3)    yes
C9 . C10 . 1.380(5)    yes
C10 . C11 . 1.385(5)    yes
C11 . C12 . 1.399(3)    yes
C13 . C14 . 1.463(3)    yes
C14 . C15 . 1.183(3)    yes
C15 . C16 . 1.372(3)    yes
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
C1 . N1 . C12 . 109.02(17)    yes
C1 . N1 . C13 . 125.5(2)    yes
C12 . N1 . C13 . 124.69(19)    yes
N1 . C1 . C2 . 108.53(18)    yes
N1 . C1 . C6 . 129.7(2)    yes
C2 . C1 . C6 . 121.72(19)    yes
C1 . C2 . C3 . 119.58(18)    yes
C1 . C2 . C7 . 106.80(16)    yes
C3 . C2 . C7 . 133.62(19)    yes
C2 . C3 . C4 . 118.8(2)    yes
C3 . C4 . C5 . 120.8(2)    yes
C4 . C5 . C6 . 122.0(2)    yes
C1 . C6 . C5 . 117.1(2)    yes
C2 . C7 . C8 . 133.1(2)    yes
C2 . C7 . C12 . 107.07(18)    yes
C8 . C7 . C12 . 119.8(2)    yes
C7 . C8 . C9 . 118.6(3)    yes
C8 . C9 . C10 . 121.4(3)    yes
C9 . C10 . C11 . 121.9(3)    yes
C10 . C11 . C12 . 117.2(3)    yes
N1 . C12 . C7 . 108.55(18)    yes
N1 . C12 . C11 . 130.3(2)    yes
C7 . C12 . C11 . 121.1(3)    yes
N1 . C13 . C14 . 112.06(19)    yes
C13 . C14 . C15 . 178.1(3)    yes
C14 . C15 . C16 . 177.0(3)    yes
N2 . C16 . C15 . 177.9(3)    yes
#****************************************************************************
#END