#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239249.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239249
loop_
_publ_author_name
'Selvanayagam, S.'
'Sridhar, B.'
'Kathiravan, S.'
'Raghunathan, R.'
_publ_section_title
;
 Methyl
 (2Z)-2-[(2-formyl-3-methyl-1H-indol-1-yl)methyl]-3-(4-methoxyphenyl)prop-2-enoate
;
_journal_coeditor_code           ZQ2219
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o431
_journal_page_last               o432
_journal_paper_doi               10.1107/S1600536814005261
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C22 H21 N O4'
_chemical_formula_moiety         'C22 H21 N O4'
_chemical_formula_sum            'C22 H21 N O4'
_chemical_formula_weight         363.40
_chemical_name_systematic
'Methyl (2Z)-2-[(2-formyl-3-methyl-1H-indol-1-yl)methyl]-3-(4-methoxyphenyl)prop-2-enoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 111.954(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6009(13)
_cell_length_b                   10.7458(11)
_cell_length_c                   14.8937(16)
_cell_measurement_reflns_used    13428
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      2.2
_cell_volume                     1870.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21494
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.017
_diffrn_reflns_theta_min         1.813
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0690P)²+0.3592P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                3214
_reflns_number_total             4462
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2219sup1.cif
_cod_data_source_block           I
_cod_database_code               2239249
_cod_database_fobs_code          2239249
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           20.13
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 1.09513(15) 0.60014(19) 0.38553(11) 0.1024(6) Uani d 1
O O2 0.73093(13) 0.23166(15) 0.23313(11) 0.0890(5) Uani d 1
O O3 0.83214(11) 0.40122(13) 0.29526(9) 0.0682(4) Uani d 1
O O4 0.44555(12) 0.52878(12) -0.32562(9) 0.0700(4) Uani d 1
N N1 0.93920(10) 0.46791(12) 0.15072(9) 0.0437(3) Uani d 1
C C1 0.97938(13) 0.39988(13) 0.09250(12) 0.0453(4) Uani d 1
C C2 0.92204(16) 0.35281(16) 0.00003(13) 0.0555(4) Uani d 1
H H2 0.8437 0.3640 -0.0321 0.067 Uiso calc 1
C C3 0.9859(2) 0.28912(17) -0.04190(16) 0.0710(6) Uani d 1
H H3 0.9499 0.2570 -0.1039 0.085 Uiso calc 1
C C4 1.1026(2) 0.27130(18) 0.00578(19) 0.0789(7) Uani d 1
H H4 1.1428 0.2267 -0.0247 0.095 Uiso calc 1
C C5 1.15958(17) 0.31737(18) 0.09595(18) 0.0709(6) Uani d 1
H H5 1.2379 0.3047 0.1270 0.085 Uiso calc 1
C C6 1.09796(14) 0.38477(15) 0.14165(13) 0.0534(4) Uani d 1
C C7 1.12943(14) 0.44737(16) 0.23098(13) 0.0559(4) Uani d 1
C C8 1.03115(13) 0.49785(15) 0.23520(12) 0.0481(4) Uani d 1
C C9 1.24838(17) 0.4581(3) 0.30555(18) 0.0886(7) Uani d 1
H H9A 1.2584 0.5388 0.3352 0.133 Uiso calc 1
H H9B 1.3028 0.4471 0.2751 0.133 Uiso calc 1
H H9C 1.2601 0.3952 0.3541 0.133 Uiso calc 1
C C10 0.81868(12) 0.50076(14) 0.12346(12) 0.0450(3) Uani d 1
H H10A 0.7900 0.5348 0.0584 0.054 Uiso calc 1
H H10B 0.8118 0.5646 0.1670 0.054 Uiso calc 1
C C11 0.74697(12) 0.39005(14) 0.12710(12) 0.0469(4) Uani d 1
C C12 0.76846(14) 0.33019(18) 0.22202(13) 0.0571(4) Uani d 1
C C13 0.8478(2) 0.3602(3) 0.39105(15) 0.0955(8) Uani d 1
H H13A 0.7749 0.3565 0.3976 0.143 Uiso calc 1
H H13B 0.8967 0.4176 0.4376 0.143 Uiso calc 1
H H13C 0.8822 0.2791 0.4020 0.143 Uiso calc 1
C C14 0.66281(13) 0.34297(16) 0.05107(12) 0.0521(4) Uani d 1
H H14 0.6321 0.2685 0.0621 0.063 Uiso calc 1
C C15 0.61153(12) 0.39180(15) -0.04761(12) 0.0483(4) Uani d 1
C C16 0.57841(15) 0.31163(16) -0.12596(13) 0.0573(4) Uani d 1
H H16 0.5927 0.2270 -0.1150 0.069 Uiso calc 1
C C17 0.52504(16) 0.35310(17) -0.21948(13) 0.0588(4) Uani d 1
H H17 0.5059 0.2973 -0.2708 0.071 Uiso calc 1
C C18 0.49998(14) 0.47814(16) -0.23680(12) 0.0514(4) Uani d 1
C C19 0.53108(14) 0.55973(15) -0.15976(13) 0.0530(4) Uani d 1
H H19 0.5147 0.6440 -0.1708 0.064 Uiso calc 1
C C20 0.58585(13) 0.51745(15) -0.06720(12) 0.0508(4) Uani d 1
H H20 0.6064 0.5739 -0.0162 0.061 Uiso calc 1
C C21 0.4105(3) 0.4468(2) -0.40614(16) 0.0957(8) Uani d 1
H H21A 0.4760 0.4035 -0.4086 0.144 Uiso calc 1
H H21B 0.3751 0.4937 -0.4646 0.144 Uiso calc 1
H H21C 0.3567 0.3877 -0.3996 0.144 Uiso calc 1
C C22 1.01886(18) 0.57581(18) 0.30950(14) 0.0651(5) Uani d 1
H H22 0.9471 0.6098 0.2981 0.078 Uiso calc 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O3 C13 117.18(17)
C18 O4 C21 117.36(15)
C1 N1 C8 108.43(13)
C1 N1 C10 123.07(13)
C8 N1 C10 128.50(13)
N1 C1 C2 130.12(15)
N1 C1 C6 107.75(14)
C2 C1 C6 122.11(15)
C3 C2 C1 117.19(18)
C3 C2 H2 121.4
C1 C2 H2 121.4
C2 C3 C4 121.7(2)
C2 C3 H3 119.1
C4 C3 H3 119.1
C5 C4 C3 121.58(18)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 118.82(19)
C4 C5 H5 120.6
C6 C5 H5 120.6
C1 C6 C7 107.79(14)
C1 C6 C5 118.56(18)
C7 C6 C5 133.63(18)
C8 C7 C6 106.93(14)
C8 C7 C9 127.16(19)
C6 C7 C9 125.90(18)
C7 C8 N1 109.09(15)
C7 C8 C22 128.42(16)
N1 C8 C22 122.41(15)
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 C11 111.97(12)
N1 C10 H10A 109.2
C11 C10 H10A 109.2
N1 C10 H10B 109.2
C11 C10 H10B 109.2
H10A C10 H10B 107.9
C14 C11 C12 116.77(15)
C14 C11 C10 124.63(15)
C12 C11 C10 118.58(14)
O2 C12 O3 122.96(17)
O2 C12 C11 125.11(18)
O3 C12 C11 111.89(15)
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C14 C15 129.15(15)
C11 C14 H14 115.4
C15 C14 H14 115.4
C16 C15 C20 116.97(16)
C16 C15 C14 120.29(15)
C20 C15 C14 122.56(15)
C17 C16 C15 122.12(16)
C17 C16 H16 118.9
C15 C16 H16 118.9
C16 C17 C18 119.69(16)
C16 C17 H17 120.2
C18 C17 H17 120.2
O4 C18 C19 116.06(15)
O4 C18 C17 124.70(15)
C19 C18 C17 119.24(16)
C20 C19 C18 120.44(16)
C20 C19 H19 119.8
C18 C19 H19 119.8
C19 C20 C15 121.53(15)
C19 C20 H20 119.2
C15 C20 H20 119.2
O4 C21 H21A 109.5
O4 C21 H21B 109.5
H21A C21 H21B 109.5
O4 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
O1 C22 C8 124.7(2)
O1 C22 H22 117.7
C8 C22 H22 117.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C22 1.209(2)
O2 C12 1.196(2)
O3 C12 1.327(2)
O3 C13 1.435(2)
O4 C18 1.356(2)
O4 C21 1.419(2)
N1 C1 1.3678(19)
N1 C8 1.3926(19)
N1 C10 1.4610(18)
C1 C2 1.390(2)
C1 C6 1.406(2)
C2 C3 1.371(3)
C2 H2 0.9300
C3 C4 1.387(3)
C3 H3 0.9300
C4 C5 1.358(3)
C4 H4 0.9300
C5 C6 1.409(3)
C5 H5 0.9300
C6 C7 1.409(3)
C7 C8 1.375(2)
C7 C9 1.499(3)
C8 C22 1.442(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.507(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C14 1.328(2)
C11 C12 1.483(2)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.464(2)
C14 H14 0.9300
C15 C16 1.383(2)
C15 C20 1.394(2)
C16 C17 1.375(2)
C16 H16 0.9300
C17 C18 1.382(2)
C17 H17 0.9300
C18 C19 1.379(2)
C19 C20 1.368(2)
C19 H19 0.9300
C20 H20 0.9300
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 H22 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9A O1 . 0.96 2.53 3.033(3) 113.0
C14 H14 O2 . 0.93 2.41 2.789(2) 104.1
C10 H10B O2 2_655 0.97 2.51 3.480(2) 173.2
C22 H22 O2 2_655 0.93 2.49 3.409(3) 171.3
C17 H17 Cg1 4_565 0.93 2.76 3.573(2) 146
C21 H21A Cg2 4_565 0.96 2.84 3.635(3) 140
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
C8 N1 C1 C2 -177.30(15)
C10 N1 C1 C2 2.3(2)
C8 N1 C1 C6 1.06(16)
C10 N1 C1 C6 -179.33(12)
N1 C1 C2 C3 178.78(15)
C6 C1 C2 C3 0.6(2)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C5 -0.8(3)
C3 C4 C5 C6 0.0(3)
N1 C1 C6 C7 -0.97(17)
C2 C1 C6 C7 177.54(14)
N1 C1 C6 C5 -179.87(14)
C2 C1 C6 C5 -1.4(2)
C4 C5 C6 C1 1.0(3)
C4 C5 C6 C7 -177.55(18)
C1 C6 C7 C8 0.51(17)
C5 C6 C7 C8 179.17(17)
C1 C6 C7 C9 -178.39(17)
C5 C6 C7 C9 0.3(3)
C6 C7 C8 N1 0.14(17)
C9 C7 C8 N1 179.02(17)
C6 C7 C8 C22 -176.54(16)
C9 C7 C8 C22 2.3(3)
C1 N1 C8 C7 -0.75(17)
C10 N1 C8 C7 179.66(13)
C1 N1 C8 C22 176.17(14)
C10 N1 C8 C22 -3.4(2)
C1 N1 C10 C11 72.45(17)
C8 N1 C10 C11 -108.02(17)
N1 C10 C11 C14 -117.11(17)
N1 C10 C11 C12 64.62(18)
C13 O3 C12 O2 -5.0(3)
C13 O3 C12 C11 172.89(16)
C14 C11 C12 O2 13.9(3)
C10 C11 C12 O2 -167.73(18)
C14 C11 C12 O3 -163.96(15)
C10 C11 C12 O3 14.4(2)
C12 C11 C14 C15 170.52(15)
C10 C11 C14 C15 -7.8(3)
C11 C14 C15 C16 142.41(18)
C11 C14 C15 C20 -42.6(2)
C20 C15 C16 C17 1.6(2)
C14 C15 C16 C17 176.85(16)
C15 C16 C17 C18 -2.0(3)
C21 O4 C18 C19 -178.81(19)
C21 O4 C18 C17 1.0(3)
C16 C17 C18 O4 -178.54(16)
C16 C17 C18 C19 1.2(3)
O4 C18 C19 C20 179.64(15)
C17 C18 C19 C20 -0.2(2)
C18 C19 C20 C15 -0.2(2)
C16 C15 C20 C19 -0.4(2)
C14 C15 C20 C19 -175.62(14)
C7 C8 C22 O1 -6.8(3)
N1 C8 C22 O1 176.90(19)
