# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_5
#TrackingRef '5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
methyl 6-propyl-9H-carbazole-3-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N1 O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.32

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   12.8565(7)
_cell_length_b                   13.8210(7)
_cell_length_c                   8.0271(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.229(5)
_cell_angle_gamma                90.00
_cell_volume                     1411.65(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4672
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      27.0

_exptl_crystal_description       plate
_exptl_crystal_colour            'color less'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crysalis PRO (Oxford Diffraction,2010)'

_exptl_special_details           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Xcalibur, sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11900
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.91
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3031
_reflns_number_gt                1989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0752P)^2^+0.1975P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3031
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1298
_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
C1 C 0.31999(15) 0.63156(15) 0.0294(3) 0.0511(5) Uani 1 1 d . . .
C2 C 0.22816(16) 0.63986(18) -0.0846(3) 0.0605(6) Uani 1 1 d . . .
C3 C 0.17704(16) 0.55630(17) -0.1410(3) 0.0576(6) Uani 1 1 d . . .
C4 C 0.21411(15) 0.46415(15) -0.0900(2) 0.0499(5) Uani 1 1 d . . .
C5 C 0.30653(14) 0.45728(15) 0.0232(2) 0.0468(5) Uani 1 1 d . . .
C6 C 0.36017(14) 0.54062(13) 0.0828(2) 0.0438(4) Uani 1 1 d . . .
C7 C 0.45627(13) 0.55864(13) 0.1973(2) 0.0416(4) Uani 1 1 d . . .
C8 C 0.53121(13) 0.50005(13) 0.2893(2) 0.0412(4) Uani 1 1 d . . .
C9 C 0.61610(13) 0.54253(13) 0.3890(2) 0.0422(4) Uani 1 1 d . . .
C10 C 0.62519(17) 0.64366(15) 0.3977(3) 0.0566(6) Uani 1 1 d . . .
C11 C 0.55237(17) 0.70273(16) 0.3077(3) 0.0639(6) Uani 1 1 d . . .
C12 C 0.46781(15) 0.65985(14) 0.2069(3) 0.0509(5) Uani 1 1 d . . .
C13 C 0.15442(18) 0.37495(19) -0.1532(3) 0.0586(6) Uani 1 1 d . . .
C14 C 0.0789(2) 0.33953(19) -0.0407(3) 0.0676(7) Uani 1 1 d . . .
C15 C 0.0206(3) 0.2485(2) -0.1016(4) 0.0795(8) Uani 1 1 d . . .
C16 C 0.69553(14) 0.47822(14) 0.4825(2) 0.0441(4) Uani 1 1 d . . .
C17 C 0.8590(2) 0.4688(2) 0.6578(3) 0.0657(6) Uani 1 1 d . . .
N1 N 0.38572(13) 0.70290(14) 0.1052(2) 0.0626(5) Uani 1 1 d . . .
O1 O 0.69040(11) 0.39110(10) 0.48804(17) 0.0577(4) Uani 1 1 d . . .
O2 O 0.77825(10) 0.52680(10) 0.56383(17) 0.0567(4) Uani 1 1 d . . .
H1 H 0.378(2) 0.769(2) 0.089(3) 0.094(9) Uiso 1 1 d . . .
H2 H 0.2055(17) 0.7014(17) -0.123(3) 0.068(6) Uiso 1 1 d . . .
H3 H 0.1123(16) 0.5621(15) -0.222(3) 0.056(5) Uiso 1 1 d . . .
H4 H 0.3324(15) 0.3924(16) 0.063(2) 0.055(6) Uiso 1 1 d . . .
H5 H 0.5239(13) 0.4280(15) 0.284(2) 0.045(5) Uiso 1 1 d . . .
H6 H 0.6815(18) 0.6709(18) 0.469(3) 0.077(7) Uiso 1 1 d . . .
H7 H 0.5598(17) 0.773(2) 0.316(3) 0.073(7) Uiso 1 1 d . . .
H8 H 0.1154(18) 0.3858(17) -0.267(3) 0.080(7) Uiso 1 1 d . . .
H9 H 0.203(2) 0.3220(19) -0.167(3) 0.091(8) Uiso 1 1 d . . .
H10 H 0.030(2) 0.395(2) -0.029(3) 0.106(10) Uiso 1 1 d . . .
H11 H 0.122(2) 0.3292(19) 0.071(4) 0.102(9) Uiso 1 1 d . . .
H12 H -0.016(2) 0.257(2) -0.216(4) 0.094(9) Uiso 1 1 d . . .
H13 H -0.029(3) 0.231(2) -0.027(4) 0.135(12) Uiso 1 1 d . . .
H14 H 0.066(3) 0.196(3) -0.118(4) 0.134(14) Uiso 1 1 d . . .
H15 H 0.912(3) 0.517(2) 0.713(4) 0.125(11) Uiso 1 1 d . . .
H16 H 0.886(2) 0.425(2) 0.583(4) 0.110(10) Uiso 1 1 d . . .
H17 H 0.829(2) 0.424(2) 0.746(4) 0.123(11) 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
C1 0.0448(10) 0.0439(11) 0.0655(12) 0.0069(9) 0.0114(9) 0.0025(9)
C2 0.0518(12) 0.0554(14) 0.0729(14) 0.0139(11) 0.0036(10) 0.0090(11)
C3 0.0436(11) 0.0701(15) 0.0573(12) 0.0071(10) 0.0014(10) 0.0014(10)
C4 0.0460(10) 0.0542(12) 0.0497(10) 0.0008(9) 0.0078(8) -0.0025(9)
C5 0.0429(10) 0.0418(12) 0.0548(11) 0.0009(8) 0.0042(8) 0.0006(8)
C6 0.0385(9) 0.0441(11) 0.0496(10) 0.0013(8) 0.0096(8) 0.0019(8)
C7 0.0401(9) 0.0342(9) 0.0521(10) -0.0022(7) 0.0124(8) -0.0038(8)
C8 0.0399(9) 0.0325(10) 0.0518(10) -0.0019(8) 0.0087(8) -0.0030(8)
C9 0.0408(9) 0.0357(10) 0.0511(10) -0.0019(8) 0.0096(8) -0.0022(8)
C10 0.0477(11) 0.0420(12) 0.0775(14) -0.0073(10) -0.0004(10) -0.0084(9)
C11 0.0562(12) 0.0313(11) 0.1003(17) -0.0043(11) -0.0023(11) -0.0054(10)
C12 0.0460(10) 0.0350(10) 0.0719(12) 0.0011(9) 0.0086(9) -0.0008(8)
C13 0.0493(11) 0.0686(15) 0.0556(13) -0.0074(10) 0.0003(10) -0.0054(11)
C14 0.0782(16) 0.0649(16) 0.0609(14) -0.0072(11) 0.0145(13) -0.0200(13)
C15 0.094(2) 0.076(2) 0.0687(17) -0.0076(14) 0.0138(16) -0.0285(17)
C16 0.0453(10) 0.0410(11) 0.0469(10) -0.0060(8) 0.0095(8) -0.0059(8)
C17 0.0563(13) 0.0593(15) 0.0750(15) -0.0038(12) -0.0131(12) 0.0045(11)
N1 0.0520(10) 0.0373(10) 0.0950(13) 0.0083(9) -0.0020(9) 0.0009(8)
O1 0.0592(9) 0.0379(9) 0.0722(9) -0.0007(6) -0.0031(7) -0.0016(6)
O2 0.0513(8) 0.0466(8) 0.0675(8) -0.0020(6) -0.0078(6) -0.0031(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 N1 1.382(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.94(2) . ?
C3 C4 1.400(3) . ?
C3 H3 0.98(2) . ?
C4 C5 1.392(3) . ?
C4 C13 1.502(3) . ?
C5 C6 1.392(3) . ?
C5 H4 0.99(2) . ?
C6 C7 1.452(3) . ?
C7 C8 1.387(2) . ?
C7 C12 1.408(3) . ?
C8 C9 1.388(2) . ?
C8 H5 1.00(2) . ?
C9 C10 1.404(3) . ?
C9 C16 1.475(3) . ?
C10 C11 1.368(3) . ?
C10 H6 0.93(2) . ?
C11 C12 1.392(3) . ?
C11 H7 0.98(3) . ?
C12 N1 1.374(3) . ?
C13 C14 1.500(3) . ?
C13 H8 0.99(3) . ?
C13 H9 0.98(3) . ?
C14 C15 1.510(3) . ?
C14 H10 1.00(3) . ?
C14 H11 1.00(3) . ?
C15 H12 0.97(3) . ?
C15 H13 0.96(4) . ?
C15 H14 0.96(4) . ?
C16 O1 1.207(2) . ?
C16 O2 1.345(2) . ?
C17 O2 1.437(3) . ?
C17 H15 1.01(3) . ?
C17 H16 0.96(3) . ?
C17 H17 1.05(3) . ?
N1 H1 0.93(3) . ?

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
N1 C1 C2 129.69(19) . . ?
N1 C1 C6 109.25(17) . . ?
C2 C1 C6 121.1(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2 122.8(14) . . ?
C1 C2 H2 119.2(14) . . ?
C2 C3 C4 122.81(19) . . ?
C2 C3 H3 118.0(12) . . ?
C4 C3 H3 119.2(12) . . ?
C5 C4 C3 118.42(19) . . ?
C5 C4 C13 120.79(19) . . ?
C3 C4 C13 120.78(19) . . ?
C6 C5 C4 120.18(19) . . ?
C6 C5 H4 120.7(12) . . ?
C4 C5 H4 119.1(12) . . ?
C5 C6 C1 119.59(17) . . ?
C5 C6 C7 133.99(17) . . ?
C1 C6 C7 106.42(16) . . ?
C8 C7 C12 119.43(17) . . ?
C8 C7 C6 134.41(16) . . ?
C12 C7 C6 106.16(16) . . ?
C7 C8 C9 119.25(16) . . ?
C7 C8 H5 120.3(10) . . ?
C9 C8 H5 120.5(10) . . ?
C8 C9 C10 120.21(18) . . ?
C8 C9 C16 117.93(16) . . ?
C10 C9 C16 121.85(17) . . ?
C11 C10 C9 121.47(19) . . ?
C11 C10 H6 119.5(15) . . ?
C9 C10 H6 119.0(15) . . ?
C10 C11 C12 118.14(19) . . ?
C10 C11 H7 120.4(13) . . ?
C12 C11 H7 121.5(13) . . ?
N1 C12 C11 129.11(18) . . ?
N1 C12 C7 109.40(17) . . ?
C11 C12 C7 121.49(18) . . ?
C4 C13 C14 114.07(19) . . ?
C4 C13 H8 110.8(14) . . ?
C14 C13 H8 108.6(13) . . ?
C4 C13 H9 110.3(15) . . ?
C14 C13 H9 107.9(15) . . ?
H8 C13 H9 104.8(19) . . ?
C13 C14 C15 114.3(2) . . ?
C13 C14 H10 105.8(16) . . ?
C15 C14 H10 112.7(16) . . ?
C13 C14 H11 105.2(15) . . ?
C15 C14 H11 111.1(16) . . ?
H10 C14 H11 107(2) . . ?
C14 C15 H12 110.7(17) . . ?
C14 C15 H13 110(2) . . ?
H12 C15 H13 110(2) . . ?
C14 C15 H14 113(2) . . ?
H12 C15 H14 101(3) . . ?
H13 C15 H14 111(3) . . ?
O1 C16 O2 121.56(17) . . ?
O1 C16 C9 125.61(16) . . ?
O2 C16 C9 112.82(16) . . ?
O2 C17 H15 104.8(18) . . ?
O2 C17 H16 109.3(18) . . ?
H15 C17 H16 114(2) . . ?
O2 C17 H17 112.0(17) . . ?
H15 C17 H17 113(2) . . ?
H16 C17 H17 105(3) . . ?
C12 N1 C1 108.77(17) . . ?
C12 N1 H1 124.7(17) . . ?
C1 N1 H1 126.5(17) . . ?
C16 O2 C17 116.01(17) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041


_database_code_depnum_ccdc_archive 'CCDC 909569'