# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Josef Breu'
_publ_contact_author_email       JOSEF.BREU@UNI-BAYREUTH.DE

_publ_section_title              
;
The crystal structure of API Montelukast
;
loop_
_publ_author_name
'Josef Breu'
'Wolfgang Milius'
'Peter Moersdorf'
'Andre Ridder'
'Juergen Thun'
'Bastian Wedel'

# Attachment 'Montelukast.CIF'

data_Montelukast
_database_code_depnum_ccdc_archive 'CCDC 714043'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(1-{[(R)-m-(E)-2-(7-chloroquinol-2-yl)vinyl)]-a-[2-(1-hydroxy-1-methylethyl)\
phenylethyl]-benzylthio}methyl)cyclopropane acetic acid
;
_chemical_name_common            
;
(1-(((R)-m-(E)-2-(7-chloroquinol-2-yl)vinyl))-a-(2-(1-hydroxy-
1-methylethyl)\ phenylethyl)-benzylthio)methyl)cyclopropane acetic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H36 Cl N O3 S'
_chemical_formula_weight         586.17
_chemical_absolute_configuration syn

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'
S S 0.1246 0.1234 '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)

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

_cell_length_a                   7.8746(16)
_cell_length_b                   21.825(4)
_cell_length_c                   17.830(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.62(3)
_cell_angle_gamma                90.00
_cell_volume                     3021.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6694
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      52

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(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  'STOE IPDS II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            40346
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         25.77
_reflns_number_total             11445
_reflns_number_gt                8103
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE IPDS II'
_computing_cell_refinement       'STOE CELL'
_computing_data_reduction        'STOE X-RED'
_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0507P)²+0.0000P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_number_reflns         11445
_refine_ls_number_parameters     747
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Cl1A Cl 1.35763(18) 0.49526(6) 0.63903(9) 0.0551(4) Uani 1 1 d . . .
S1A S 0.99217(15) 1.14321(5) 0.82276(7) 0.0385(3) Uani 1 1 d . . .
O1A O 1.0012(4) 1.23646(15) 1.08329(19) 0.0452(8) Uani 1 1 d . . .
H1 H 1.0621 1.2308 1.1261 0.068 Uiso 1 1 calc R . .
O2A O 1.1011(5) 1.14497(19) 1.0578(2) 0.0638(11) Uani 1 1 d . . .
O3A O 1.3207(5) 1.04666(18) 0.44116(18) 0.0497(9) Uani 1 1 d . . .
H2 H 1.4021 1.0233 0.4350 0.075 Uiso 1 1 calc R . .
N1A N 1.2303(5) 0.70986(17) 0.7241(2) 0.0330(9) Uani 1 1 d . . .
C1A C 1.0003(6) 1.1868(2) 1.0424(3) 0.0372(11) Uani 1 1 d . . .
C2A C 0.8552(6) 1.1870(2) 0.9757(3) 0.0400(11) Uani 1 1 d . . .
H3A H 0.7512 1.2039 0.9926 0.048 Uiso 1 1 calc R . .
H3B H 0.8862 1.2148 0.9362 0.048 Uiso 1 1 calc R . .
C3A C 0.8120(6) 1.1252(2) 0.9407(3) 0.0359(11) Uani 1 1 d . . .
C4A C 0.7093(6) 1.0819(2) 0.9819(3) 0.0439(12) Uani 1 1 d . . .
H4A H 0.7363 1.0376 0.9808 0.053 Uiso 1 1 calc R . .
H4B H 0.6746 1.0964 1.0297 0.053 Uiso 1 1 calc R . .
C5A C 0.6265(6) 1.1113(2) 0.9092(3) 0.0457(12) Uani 1 1 d . . .
H5A H 0.5405 1.1439 0.9123 0.055 Uiso 1 1 calc R . .
H5B H 0.6021 1.0852 0.8633 0.055 Uiso 1 1 calc R . .
C6A C 0.9446(7) 1.0961(2) 0.9014(3) 0.0426(12) Uani 1 1 d . . .
H6A H 0.9028 1.0555 0.8817 0.051 Uiso 1 1 calc R . .
H6B H 1.0516 1.0898 0.9385 0.051 Uiso 1 1 calc R . .
C7A C 1.1419(6) 1.0908(2) 0.7884(3) 0.0349(10) Uani 1 1 d . . .
H7 H 1.2345 1.0808 0.8322 0.042 Uiso 1 1 calc R . .
C8A C 1.2274(6) 1.1231(2) 0.7279(3) 0.0361(11) Uani 1 1 d . . .
H8A H 1.2926 1.1592 0.7509 0.043 Uiso 1 1 calc R . .
H8B H 1.1373 1.1378 0.6863 0.043 Uiso 1 1 calc R . .
C9A C 1.3499(6) 1.0797(2) 0.6952(2) 0.0340(10) Uani 1 1 d . . .
H9A H 1.4318 1.0620 0.7379 0.041 Uiso 1 1 calc R . .
H9B H 1.2817 1.0455 0.6690 0.041 Uiso 1 1 calc R . .
C10A C 1.4523(5) 1.10951(19) 0.6397(2) 0.0304(10) Uani 1 1 d . . .
C11A C 1.4326(6) 1.0951(2) 0.5619(2) 0.0314(10) Uani 1 1 d . . .
C12A C 1.3043(6) 1.0478(2) 0.5201(3) 0.0363(10) Uani 1 1 d . . .
C13A C 1.3394(7) 0.9831(2) 0.5505(3) 0.0496(13) Uani 1 1 d . . .
H10A H 1.2706 0.9539 0.5164 0.074 Uiso 1 1 calc R . .
H10B H 1.3083 0.9801 0.6014 0.074 Uiso 1 1 calc R . .
H10C H 1.4620 0.9737 0.5535 0.074 Uiso 1 1 calc R . .
C14A C 1.1209(6) 1.0668(2) 0.5190(3) 0.0451(12) Uani 1 1 d . . .
H11A H 1.0990 1.1056 0.4913 0.068 Uiso 1 1 calc R . .
H11B H 1.1004 1.0722 0.5714 0.068 Uiso 1 1 calc R . .
H11C H 1.0435 1.0352 0.4938 0.068 Uiso 1 1 calc R . .
C15A C 1.5406(6) 1.1259(2) 0.5195(3) 0.0425(12) Uani 1 1 d . . .
H12 H 1.5335 1.1165 0.4670 0.051 Uiso 1 1 calc R . .
C16A C 1.6586(6) 1.1700(2) 0.5522(3) 0.0458(13) Uani 1 1 d . . .
H13 H 1.7270 1.1913 0.5216 0.055 Uiso 1 1 calc R . .
C17A C 1.6758(6) 1.1825(2) 0.6276(3) 0.0390(11) Uani 1 1 d . . .
H14 H 1.7575 1.2120 0.6500 0.047 Uiso 1 1 calc R . .
C18A C 1.5748(5) 1.1524(2) 0.6710(3) 0.0340(10) Uani 1 1 d . . .
H15 H 1.5887 1.1610 0.7239 0.041 Uiso 1 1 calc R . .
C19A C 1.0591(5) 1.0318(2) 0.7593(2) 0.0298(10) Uani 1 1 d . . .
C20A C 1.1316(6) 0.9766(2) 0.7864(3) 0.0359(10) Uani 1 1 d . . .
H16 H 1.2245 0.9772 0.8279 0.043 Uiso 1 1 calc R . .
C21A C 1.0742(5) 0.9206(2) 0.7554(3) 0.0334(10) Uani 1 1 d . . .
C22A C 0.9386(6) 0.9208(2) 0.6946(3) 0.0366(11) Uani 1 1 d . . .
H17 H 0.8981 0.8832 0.6715 0.044 Uiso 1 1 calc R . .
C23A C 0.8618(6) 0.9752(2) 0.6674(3) 0.0390(11) Uani 1 1 d . . .
H18 H 0.7679 0.9747 0.6263 0.047 Uiso 1 1 calc R . .
C24A C 0.9213(6) 1.0303(2) 0.6997(3) 0.0342(11) Uani 1 1 d . . .
H19 H 0.8673 1.0675 0.6810 0.041 Uiso 1 1 calc R . .
C25A C 1.1637(6) 0.8642(2) 0.7851(3) 0.0375(11) Uani 1 1 d . . .
H20 H 1.2401 0.8669 0.8322 0.045 Uiso 1 1 calc R . .
C26A C 1.1464(6) 0.8100(2) 0.7513(3) 0.0353(11) Uani 1 1 d . . .
H21 H 1.0600 0.8066 0.7074 0.042 Uiso 1 1 calc R . .
C27A C 1.2469(6) 0.7547(2) 0.7748(3) 0.0340(11) Uani 1 1 d . . .
C28A C 1.3574(6) 0.7496(2) 0.8465(3) 0.0361(11) Uani 1 1 d . . .
H22 H 1.3643 0.7822 0.8823 0.043 Uiso 1 1 calc R . .
C29A C 1.4529(6) 0.6979(2) 0.8637(3) 0.0379(11) Uani 1 1 d . . .
H23 H 1.5287 0.6946 0.9110 0.046 Uiso 1 1 calc R . .
C30A C 1.4383(5) 0.6491(2) 0.8105(3) 0.0347(10) Uani 1 1 d . . .
C31A C 1.5308(6) 0.5937(2) 0.8236(3) 0.0399(12) Uani 1 1 d . . .
H24 H 1.6111 0.5885 0.8693 0.048 Uiso 1 1 calc R . .
C32A C 1.5065(6) 0.5478(2) 0.7720(3) 0.0432(12) Uani 1 1 d . . .
H25 H 1.5667 0.5102 0.7818 0.052 Uiso 1 1 calc R . .
C33A C 1.3917(6) 0.5562(2) 0.7038(3) 0.0373(11) Uani 1 1 d . . .
C34A C 1.3016(6) 0.6093(2) 0.6874(3) 0.0381(11) Uani 1 1 d . . .
H26 H 1.2253 0.6139 0.6405 0.046 Uiso 1 1 calc R . .
C35A C 1.3240(5) 0.6572(2) 0.7412(3) 0.0333(10) Uani 1 1 d . . .
Cl1B Cl 0.63987(16) 0.94631(5) 0.85354(7) 0.0432(3) Uani 1 1 d . . .
S1B S 0.83459(13) 0.35083(5) 0.60548(6) 0.0321(2) Uani 1 1 d . . .
O1B O 0.9359(5) 0.21152(16) 0.4268(2) 0.0498(9) Uani 1 1 d . . .
H27 H 0.8901 0.2202 0.3821 0.075 Uiso 1 1 calc R . .
O2B O 1.0641(6) 0.30172(19) 0.4197(2) 0.0657(11) Uani 1 1 d . . .
O3B O 0.7636(4) 0.44293(17) 0.87585(19) 0.0487(9) Uani 1 1 d . . .
H28 H 0.8511 0.4655 0.8833 0.073 Uiso 1 1 calc R . .
N1B N 0.8076(4) 0.73250(16) 0.7807(2) 0.0293(8) Uani 1 1 d . . .
C1B C 1.0270(6) 0.2586(2) 0.4572(3) 0.0365(11) Uani 1 1 d . . .
C2B C 1.0934(6) 0.2522(2) 0.5413(3) 0.0385(11) Uani 1 1 d . . .
H29A H 1.1867 0.2213 0.5487 0.046 Uiso 1 1 calc R . .
H29B H 0.9991 0.2367 0.5665 0.046 Uiso 1 1 calc R . .
C3B C 1.1613(6) 0.3113(2) 0.5794(3) 0.0349(10) Uani 1 1 d . . .
C4B C 1.2936(6) 0.3056(3) 0.6503(3) 0.0499(13) Uani 1 1 d . . .
H30A H 1.2924 0.3366 0.6907 0.060 Uiso 1 1 calc R . .
H30B H 1.3268 0.2638 0.6689 0.060 Uiso 1 1 calc R . .
C5B C 1.3473(6) 0.3257(3) 0.5786(3) 0.0551(15) Uani 1 1 d . . .
H31A H 1.4139 0.2965 0.5525 0.066 Uiso 1 1 calc R . .
H31B H 1.3795 0.3693 0.5743 0.066 Uiso 1 1 calc R . .
C6B C 1.0379(6) 0.3644(2) 0.5737(3) 0.0350(10) Uani 1 1 d . . .
H32A H 1.0133 0.3777 0.5198 0.042 Uiso 1 1 calc R . .
H32B H 1.0963 0.3989 0.6036 0.042 Uiso 1 1 calc R . .
C7B C 0.8972(5) 0.3506(2) 0.7086(2) 0.0316(9) Uani 1 1 d . . .
H33 H 0.9782 0.3157 0.7230 0.038 Uiso 1 1 calc R . .
C8B C 0.7351(5) 0.3396(2) 0.7441(2) 0.0315(10) Uani 1 1 d . . .
H34A H 0.6673 0.3779 0.7418 0.038 Uiso 1 1 calc R . .
H34B H 0.6629 0.3081 0.7142 0.038 Uiso 1 1 calc R . .
C9B C 0.7789(6) 0.3189(2) 0.8256(3) 0.0348(10) Uani 1 1 d . . .
H35A H 0.8723 0.3454 0.8518 0.042 Uiso 1 1 calc R . .
H35B H 0.8252 0.2767 0.8260 0.042 Uiso 1 1 calc R . .
C10B C 0.6328(6) 0.3192(2) 0.8720(2) 0.0318(10) Uani 1 1 d . . .
C11B C 0.6141(5) 0.3621(2) 0.9290(3) 0.0361(11) Uani 1 1 d . . .
C12B C 0.7358(6) 0.4161(2) 0.9487(3) 0.0413(11) Uani 1 1 d . . .
C13B C 0.6641(7) 0.4680(3) 0.9901(3) 0.0585(15) Uani 1 1 d . . .
H36A H 0.7452 0.5024 0.9957 0.088 Uiso 1 1 calc R . .
H36B H 0.6471 0.4539 1.0406 0.088 Uiso 1 1 calc R . .
H36C H 0.5535 0.4812 0.9610 0.088 Uiso 1 1 calc R . .
C14B C 0.9085(6) 0.3937(3) 0.9952(3) 0.0543(14) Uani 1 1 d . . .
H37A H 0.9581 0.3620 0.9665 0.081 Uiso 1 1 calc R . .
H37B H 0.8880 0.3767 1.0438 0.081 Uiso 1 1 calc R . .
H37C H 0.9887 0.4282 1.0048 0.081 Uiso 1 1 calc R . .
C15B C 0.4789(5) 0.3533(2) 0.9690(2) 0.0392(11) Uani 1 1 d . . .
H38 H 0.4663 0.3812 1.0086 0.047 Uiso 1 1 calc R . .
C16B C 0.3623(6) 0.3059(2) 0.9541(3) 0.0398(11) Uani 1 1 d . . .
H39 H 0.2732 0.3012 0.9836 0.048 Uiso 1 1 calc R . .
C17B C 0.3757(6) 0.2654(2) 0.8964(3) 0.0443(12) Uani 1 1 d . . .
H40 H 0.2950 0.2331 0.8845 0.053 Uiso 1 1 calc R . .
C18B C 0.5102(6) 0.2730(2) 0.8557(3) 0.0361(11) Uani 1 1 d . . .
H41 H 0.5188 0.2456 0.8151 0.043 Uiso 1 1 calc R . .
C19B C 0.9851(5) 0.4092(2) 0.7411(2) 0.0276(9) Uani 1 1 d . . .
C20B C 0.9154(5) 0.46575(19) 0.7167(2) 0.0270(9) Uani 1 1 d . . .
H42 H 0.8241 0.4674 0.6745 0.032 Uiso 1 1 calc R . .
C21B C 0.9771(5) 0.52026(19) 0.7529(2) 0.0271(9) Uani 1 1 d . . .
C22B C 1.1128(5) 0.5171(2) 0.8141(3) 0.0334(10) Uani 1 1 d . . .
H43 H 1.1548 0.5534 0.8402 0.040 Uiso 1 1 calc R . .
C23B C 1.1858(5) 0.4613(2) 0.8366(3) 0.0357(11) Uani 1 1 d . . .
H44 H 1.2792 0.4594 0.8779 0.043 Uiso 1 1 calc R . .
C24B C 1.1241(5) 0.4078(2) 0.7996(2) 0.0322(10) Uani 1 1 d . . .
H45 H 1.1781 0.3698 0.8147 0.039 Uiso 1 1 calc R . .
C25B C 0.8924(5) 0.5779(2) 0.7254(3) 0.0312(10) Uani 1 1 d . . .
H46 H 0.8210 0.5764 0.6769 0.037 Uiso 1 1 calc R . .
C26B C 0.9035(5) 0.63143(19) 0.7601(2) 0.0297(10) Uani 1 1 d . . .
H47 H 0.9817 0.6350 0.8067 0.036 Uiso 1 1 calc R . .
C27B C 0.8040(5) 0.6859(2) 0.7320(3) 0.0300(10) Uani 1 1 d . . .
C28B C 0.7052(5) 0.6885(2) 0.6589(3) 0.0333(10) Uani 1 1 d . . .
H48 H 0.7069 0.6552 0.6248 0.040 Uiso 1 1 calc R . .
C29B C 0.6064(6) 0.7391(2) 0.6365(3) 0.0374(11) Uani 1 1 d . . .
H49 H 0.5364 0.7402 0.5877 0.045 Uiso 1 1 calc R . .
C30B C 0.6091(5) 0.7897(2) 0.6868(3) 0.0310(10) Uani 1 1 d . . .
C31B C 0.5148(6) 0.8435(2) 0.6683(3) 0.0357(10) Uani 1 1 d . . .
H50 H 0.4437 0.8473 0.6199 0.043 Uiso 1 1 calc R . .
C32B C 0.5241(6) 0.8908(2) 0.7194(3) 0.0369(11) Uani 1 1 d . . .
H51 H 0.4604 0.9274 0.7066 0.044 Uiso 1 1 calc R . .
C33B C 0.6281(6) 0.8846(2) 0.7905(3) 0.0346(11) Uani 1 1 d . . .
C34B C 0.7220(5) 0.83339(19) 0.8108(2) 0.0303(10) Uani 1 1 d . . .
H52 H 0.7927 0.8305 0.8593 0.036 Uiso 1 1 calc R . .
C35B C 0.7129(5) 0.78451(19) 0.7585(3) 0.0296(10) Uani 1 1 d . . .


_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
Cl1A C33A 1.754(5) . ?
S1A C7A 1.822(5) . ?
S1A C6A 1.827(5) . ?
O1A C1A 1.306(6) . ?
O1A H1 0.8400 . ?
O2A C1A 1.210(6) . ?
O3A C12A 1.434(5) . ?
O3A H2 0.8400 . ?
N1A C27A 1.324(6) . ?
N1A C35A 1.373(6) . ?
C1A C2A 1.504(7) . ?
C2A C3A 1.503(7) . ?
C2A H3A 0.9900 . ?
C2A H3B 0.9900 . ?
C3A C6A 1.492(6) . ?
C3A C5A 1.505(6) . ?
C3A C4A 1.512(6) . ?
C4A C5A 1.494(7) . ?
C4A H4A 0.9900 . ?
C4A H4B 0.9900 . ?
C5A H5A 0.9900 . ?
C5A H5B 0.9900 . ?
C6A H6A 0.9900 . ?
C6A H6B 0.9900 . ?
C7A C19A 1.495(6) . ?
C7A C8A 1.535(6) . ?
C7A H7 1.0000 . ?
C8A C9A 1.535(6) . ?
C8A H8A 0.9900 . ?
C8A H8B 0.9900 . ?
C9A C10A 1.523(6) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C10A C18A 1.392(6) . ?
C10A C11A 1.405(6) . ?
C11A C15A 1.401(6) . ?
C11A C12A 1.547(6) . ?
C12A C14A 1.500(6) . ?
C12A C13A 1.521(7) . ?
C13A H10A 0.9800 . ?
C13A H10B 0.9800 . ?
C13A H10C 0.9800 . ?
C14A H11A 0.9800 . ?
C14A H11B 0.9800 . ?
C14A H11C 0.9800 . ?
C15A C16A 1.396(7) . ?
C15A H12 0.9500 . ?
C16A C17A 1.355(7) . ?
C16A H13 0.9500 . ?
C17A C18A 1.367(6) . ?
C17A H14 0.9500 . ?
C18A H15 0.9500 . ?
C19A C20A 1.385(6) . ?
C19A C24A 1.386(6) . ?
C20A C21A 1.386(6) . ?
C20A H16 0.9500 . ?
C21A C22A 1.389(7) . ?
C21A C25A 1.472(6) . ?
C22A C23A 1.382(7) . ?
C22A H17 0.9500 . ?
C23A C24A 1.381(7) . ?
C23A H18 0.9500 . ?
C24A H19 0.9500 . ?
C25A C26A 1.325(6) . ?
C25A H20 0.9500 . ?
C26A C27A 1.464(6) . ?
C26A H21 0.9500 . ?
C27A C28A 1.426(7) . ?
C28A C29A 1.362(7) . ?
C28A H22 0.9500 . ?
C29A C30A 1.418(7) . ?
C29A H23 0.9500 . ?
C30A C31A 1.411(7) . ?
C30A C35A 1.413(6) . ?
C31A C32A 1.353(7) . ?
C31A H24 0.9500 . ?
C32A C33A 1.400(7) . ?
C32A H25 0.9500 . ?
C33A C34A 1.364(7) . ?
C34A C35A 1.410(7) . ?
C34A H26 0.9500 . ?
Cl1B C33B 1.747(5) . ?
S1B C6B 1.810(4) . ?
S1B C7B 1.823(4) . ?
O1B C1B 1.317(5) . ?
O1B H27 0.8400 . ?
O2B C1B 1.218(6) . ?
O3B C12B 1.473(6) . ?
O3B H28 0.8400 . ?
N1B C27B 1.334(6) . ?
N1B C35B 1.379(5) . ?
C1B C2B 1.509(7) . ?
C2B C3B 1.515(6) . ?
C2B H29A 0.9900 . ?
C2B H29B 0.9900 . ?
C3B C5B 1.500(7) . ?
C3B C4B 1.502(7) . ?
C3B C6B 1.505(6) . ?
C4B C5B 1.479(8) . ?
C4B H30A 0.9900 . ?
C4B H30B 0.9900 . ?
C5B H31A 0.9900 . ?
C5B H31B 0.9900 . ?
C6B H32A 0.9900 . ?
C6B H32B 0.9900 . ?
C7B C19B 1.522(6) . ?
C7B C8B 1.536(6) . ?
C7B H33 1.0000 . ?
C8B C9B 1.506(6) . ?
C8B H34A 0.9900 . ?
C8B H34B 0.9900 . ?
C9B C10B 1.524(6) . ?
C9B H35A 0.9900 . ?
C9B H35B 0.9900 . ?
C10B C18B 1.393(6) . ?
C10B C11B 1.407(6) . ?
C11B C15B 1.391(6) . ?
C11B C12B 1.523(7) . ?
C12B C13B 1.512(7) . ?
C12B C14B 1.549(7) . ?
C13B H36A 0.9800 . ?
C13B H36B 0.9800 . ?
C13B H36C 0.9800 . ?
C14B H37A 0.9800 . ?
C14B H37B 0.9800 . ?
C14B H37C 0.9800 . ?
C15B C16B 1.380(7) . ?
C15B H38 0.9500 . ?
C16B C17B 1.373(7) . ?
C16B H39 0.9500 . ?
C17B C18B 1.390(7) . ?
C17B H40 0.9500 . ?
C18B H41 0.9500 . ?
C19B C24B 1.380(6) . ?
C19B C20B 1.390(6) . ?
C20B C21B 1.401(6) . ?
C20B H42 0.9500 . ?
C21B C22B 1.396(6) . ?
C21B C25B 1.468(6) . ?
C22B C23B 1.378(6) . ?
C22B H43 0.9500 . ?
C23B C24B 1.389(6) . ?
C23B H44 0.9500 . ?
C24B H45 0.9500 . ?
C25B C26B 1.319(6) . ?
C25B H46 0.9500 . ?
C26B C27B 1.465(6) . ?
C26B H47 0.9500 . ?
C27B C28B 1.404(6) . ?
C28B C29B 1.370(7) . ?
C28B H48 0.9500 . ?
C29B C30B 1.422(7) . ?
C29B H49 0.9500 . ?
C30B C31B 1.399(6) . ?
C30B C35B 1.402(6) . ?
C31B C32B 1.371(7) . ?
C31B H50 0.9500 . ?
C32B C33B 1.396(7) . ?
C32B H51 0.9500 . ?
C33B C34B 1.356(6) . ?
C34B C35B 1.410(6) . ?
C34B H52 0.9500 . ?

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
C7A S1A C6A 97.6(2) . . ?
C1A O1A H1 109.5 . . ?
C12A O3A H2 109.5 . . ?
C27A N1A C35A 118.7(4) . . ?
O2A C1A O1A 123.9(5) . . ?
O2A C1A C2A 124.4(4) . . ?
O1A C1A C2A 111.7(4) . . ?
C3A C2A C1A 114.5(4) . . ?
C3A C2A H3A 108.6 . . ?
C1A C2A H3A 108.6 . . ?
C3A C2A H3B 108.6 . . ?
C1A C2A H3B 108.6 . . ?
H3A C2A H3B 107.6 . . ?
C6A C3A C2A 116.7(4) . . ?
C6A C3A C5A 116.8(4) . . ?
C2A C3A C5A 118.3(4) . . ?
C6A C3A C4A 115.8(4) . . ?
C2A C3A C4A 117.5(4) . . ?
C5A C3A C4A 59.4(3) . . ?
C5A C4A C3A 60.1(3) . . ?
C5A C4A H4A 117.8 . . ?
C3A C4A H4A 117.8 . . ?
C5A C4A H4B 117.8 . . ?
C3A C4A H4B 117.8 . . ?
H4A C4A H4B 114.9 . . ?
C4A C5A C3A 60.5(3) . . ?
C4A C5A H5A 117.7 . . ?
C3A C5A H5A 117.7 . . ?
C4A C5A H5B 117.7 . . ?
C3A C5A H5B 117.7 . . ?
H5A C5A H5B 114.8 . . ?
C3A C6A S1A 111.7(3) . . ?
C3A C6A H6A 109.3 . . ?
S1A C6A H6A 109.3 . . ?
C3A C6A H6B 109.3 . . ?
S1A C6A H6B 109.3 . . ?
H6A C6A H6B 107.9 . . ?
C19A C7A C8A 111.7(4) . . ?
C19A C7A S1A 112.8(3) . . ?
C8A C7A S1A 109.4(3) . . ?
C19A C7A H7 107.6 . . ?
C8A C7A H7 107.6 . . ?
S1A C7A H7 107.6 . . ?
C7A C8A C9A 111.0(4) . . ?
C7A C8A H8A 109.4 . . ?
C9A C8A H8A 109.4 . . ?
C7A C8A H8B 109.4 . . ?
C9A C8A H8B 109.4 . . ?
H8A C8A H8B 108.0 . . ?
C10A C9A C8A 114.7(4) . . ?
C10A C9A H9A 108.6 . . ?
C8A C9A H9A 108.6 . . ?
C10A C9A H9B 108.6 . . ?
C8A C9A H9B 108.6 . . ?
H9A C9A H9B 107.6 . . ?
C18A C10A C11A 120.0(4) . . ?
C18A C10A C9A 115.7(4) . . ?
C11A C10A C9A 124.2(4) . . ?
C15A C11A C10A 116.7(4) . . ?
C15A C11A C12A 117.8(4) . . ?
C10A C11A C12A 125.5(4) . . ?
O3A C12A C14A 103.7(4) . . ?
O3A C12A C13A 107.1(4) . . ?
C14A C12A C13A 112.3(4) . . ?
O3A C12A C11A 109.1(4) . . ?
C14A C12A C11A 111.7(4) . . ?
C13A C12A C11A 112.5(4) . . ?
C12A C13A H10A 109.5 . . ?
C12A C13A H10B 109.5 . . ?
H10A C13A H10B 109.5 . . ?
C12A C13A H10C 109.5 . . ?
H10A C13A H10C 109.5 . . ?
H10B C13A H10C 109.5 . . ?
C12A C14A H11A 109.5 . . ?
C12A C14A H11B 109.5 . . ?
H11A C14A H11B 109.5 . . ?
C12A C14A H11C 109.5 . . ?
H11A C14A H11C 109.5 . . ?
H11B C14A H11C 109.5 . . ?
C16A C15A C11A 121.8(4) . . ?
C16A C15A H12 119.1 . . ?
C11A C15A H12 119.1 . . ?
C17A C16A C15A 120.2(4) . . ?
C17A C16A H13 119.9 . . ?
C15A C16A H13 119.9 . . ?
C16A C17A C18A 119.5(4) . . ?
C16A C17A H14 120.2 . . ?
C18A C17A H14 120.2 . . ?
C17A C18A C10A 121.8(4) . . ?
C17A C18A H15 119.1 . . ?
C10A C18A H15 119.1 . . ?
C20A C19A C24A 118.0(4) . . ?
C20A C19A C7A 119.8(4) . . ?
C24A C19A C7A 121.8(4) . . ?
C19A C20A C21A 122.7(4) . . ?
C19A C20A H16 118.6 . . ?
C21A C20A H16 118.6 . . ?
C20A C21A C22A 117.7(4) . . ?
C20A C21A C25A 119.3(4) . . ?
C22A C21A C25A 122.9(4) . . ?
C23A C22A C21A 120.7(5) . . ?
C23A C22A H17 119.6 . . ?
C21A C22A H17 119.6 . . ?
C24A C23A C22A 120.2(4) . . ?
C24A C23A H18 119.9 . . ?
C22A C23A H18 119.9 . . ?
C23A C24A C19A 120.5(4) . . ?
C23A C24A H19 119.7 . . ?
C19A C24A H19 119.7 . . ?
C26A C25A C21A 125.3(5) . . ?
C26A C25A H20 117.4 . . ?
C21A C25A H20 117.4 . . ?
C25A C26A C27A 126.6(5) . . ?
C25A C26A H21 116.7 . . ?
C27A C26A H21 116.7 . . ?
N1A C27A C28A 122.0(4) . . ?
N1A C27A C26A 115.3(4) . . ?
C28A C27A C26A 122.8(4) . . ?
C29A C28A C27A 119.9(4) . . ?
C29A C28A H22 120.0 . . ?
C27A C28A H22 120.0 . . ?
C28A C29A C30A 119.4(4) . . ?
C28A C29A H23 120.3 . . ?
C30A C29A H23 120.3 . . ?
C31A C30A C35A 119.2(5) . . ?
C31A C30A C29A 123.4(4) . . ?
C35A C30A C29A 117.4(4) . . ?
C32A C31A C30A 120.7(5) . . ?
C32A C31A H24 119.6 . . ?
C30A C31A H24 119.6 . . ?
C31A C32A C33A 119.4(5) . . ?
C31A C32A H25 120.3 . . ?
C33A C32A H25 120.3 . . ?
C34A C33A C32A 122.4(5) . . ?
C34A C33A Cl1A 119.0(4) . . ?
C32A C33A Cl1A 118.5(4) . . ?
C33A C34A C35A 118.7(5) . . ?
C33A C34A H26 120.6 . . ?
C35A C34A H26 120.6 . . ?
N1A C35A C34A 117.9(4) . . ?
N1A C35A C30A 122.6(4) . . ?
C34A C35A C30A 119.5(4) . . ?
C6B S1B C7B 102.3(2) . . ?
C1B O1B H27 109.5 . . ?
C12B O3B H28 109.5 . . ?
C27B N1B C35B 119.3(4) . . ?
O2B C1B O1B 122.7(5) . . ?
O2B C1B C2B 122.9(4) . . ?
O1B C1B C2B 114.2(4) . . ?
C1B C2B C3B 113.9(4) . . ?
C1B C2B H29A 108.8 . . ?
C3B C2B H29A 108.8 . . ?
C1B C2B H29B 108.8 . . ?
C3B C2B H29B 108.8 . . ?
H29A C2B H29B 107.7 . . ?
C5B C3B C4B 59.0(3) . . ?
C5B C3B C6B 117.3(4) . . ?
C4B C3B C6B 118.1(4) . . ?
C5B C3B C2B 116.5(4) . . ?
C4B C3B C2B 116.7(4) . . ?
C6B C3B C2B 116.7(4) . . ?
C5B C4B C3B 60.4(3) . . ?
C5B C4B H30A 117.7 . . ?
C3B C4B H30A 117.7 . . ?
C5B C4B H30B 117.7 . . ?
C3B C4B H30B 117.7 . . ?
H30A C4B H30B 114.9 . . ?
C4B C5B C3B 60.6(3) . . ?
C4B C5B H31A 117.7 . . ?
C3B C5B H31A 117.7 . . ?
C4B C5B H31B 117.7 . . ?
C3B C5B H31B 117.7 . . ?
H31A C5B H31B 114.8 . . ?
C3B C6B S1B 116.6(3) . . ?
C3B C6B H32A 108.1 . . ?
S1B C6B H32A 108.1 . . ?
C3B C6B H32B 108.1 . . ?
S1B C6B H32B 108.1 . . ?
H32A C6B H32B 107.3 . . ?
C19B C7B C8B 109.4(3) . . ?
C19B C7B S1B 114.3(3) . . ?
C8B C7B S1B 108.2(3) . . ?
C19B C7B H33 108.3 . . ?
C8B C7B H33 108.3 . . ?
S1B C7B H33 108.3 . . ?
C9B C8B C7B 111.9(4) . . ?
C9B C8B H34A 109.2 . . ?
C7B C8B H34A 109.2 . . ?
C9B C8B H34B 109.2 . . ?
C7B C8B H34B 109.2 . . ?
H34A C8B H34B 107.9 . . ?
C8B C9B C10B 116.7(4) . . ?
C8B C9B H35A 108.1 . . ?
C10B C9B H35A 108.1 . . ?
C8B C9B H35B 108.1 . . ?
C10B C9B H35B 108.1 . . ?
H35A C9B H35B 107.3 . . ?
C18B C10B C11B 118.7(4) . . ?
C18B C10B C9B 116.3(4) . . ?
C11B C10B C9B 125.0(4) . . ?
C15B C11B C10B 117.4(4) . . ?
C15B C11B C12B 119.7(4) . . ?
C10B C11B C12B 122.9(4) . . ?
O3B C12B C13B 104.8(4) . . ?
O3B C12B C11B 106.6(4) . . ?
C13B C12B C11B 114.8(4) . . ?
O3B C12B C14B 110.6(4) . . ?
C13B C12B C14B 109.9(4) . . ?
C11B C12B C14B 110.0(4) . . ?
C12B C13B H36A 109.5 . . ?
C12B C13B H36B 109.5 . . ?
H36A C13B H36B 109.5 . . ?
C12B C13B H36C 109.5 . . ?
H36A C13B H36C 109.5 . . ?
H36B C13B H36C 109.5 . . ?
C12B C14B H37A 109.5 . . ?
C12B C14B H37B 109.5 . . ?
H37A C14B H37B 109.5 . . ?
C12B C14B H37C 109.5 . . ?
H37A C14B H37C 109.5 . . ?
H37B C14B H37C 109.5 . . ?
C16B C15B C11B 123.1(5) . . ?
C16B C15B H38 118.5 . . ?
C11B C15B H38 118.5 . . ?
C17B C16B C15B 119.7(4) . . ?
C17B C16B H39 120.2 . . ?
C15B C16B H39 120.2 . . ?
C16B C17B C18B 118.4(5) . . ?
C16B C17B H40 120.8 . . ?
C18B C17B H40 120.8 . . ?
C17B C18B C10B 122.7(5) . . ?
C17B C18B H41 118.7 . . ?
C10B C18B H41 118.7 . . ?
C24B C19B C20B 118.6(4) . . ?
C24B C19B C7B 121.4(4) . . ?
C20B C19B C7B 119.7(4) . . ?
C19B C20B C21B 121.4(4) . . ?
C19B C20B H42 119.3 . . ?
C21B C20B H42 119.3 . . ?
C22B C21B C20B 118.7(4) . . ?
C22B C21B C25B 123.3(4) . . ?
C20B C21B C25B 118.0(4) . . ?
C23B C22B C21B 119.9(4) . . ?
C23B C22B H43 120.0 . . ?
C21B C22B H43 120.0 . . ?
C22B C23B C24B 120.6(4) . . ?
C22B C23B H44 119.7 . . ?
C24B C23B H44 119.7 . . ?
C19B C24B C23B 120.7(4) . . ?
C19B C24B H45 119.7 . . ?
C23B C24B H45 119.7 . . ?
C26B C25B C21B 127.7(4) . . ?
C26B C25B H46 116.1 . . ?
C21B C25B H46 116.1 . . ?
C25B C26B C27B 124.7(4) . . ?
C25B C26B H47 117.7 . . ?
C27B C26B H47 117.7 . . ?
N1B C27B C28B 121.4(4) . . ?
N1B C27B C26B 116.4(4) . . ?
C28B C27B C26B 122.2(4) . . ?
C29B C28B C27B 120.2(4) . . ?
C29B C28B H48 119.9 . . ?
C27B C28B H48 119.9 . . ?
C28B C29B C30B 119.6(4) . . ?
C28B C29B H49 120.2 . . ?
C30B C29B H49 120.2 . . ?
C31B C30B C35B 119.3(4) . . ?
C31B C30B C29B 123.5(4) . . ?
C35B C30B C29B 117.2(4) . . ?
C32B C31B C30B 120.5(4) . . ?
C32B C31B H50 119.8 . . ?
C30B C31B H50 119.8 . . ?
C31B C32B C33B 119.3(4) . . ?
C31B C32B H51 120.4 . . ?
C33B C32B H51 120.4 . . ?
C34B C33B C32B 122.2(4) . . ?
C34B C33B Cl1B 119.7(4) . . ?
C32B C33B Cl1B 118.0(4) . . ?
C33B C34B C35B 118.8(4) . . ?
C33B C34B H52 120.6 . . ?
C35B C34B H52 120.6 . . ?
N1B C35B C30B 122.2(4) . . ?
N1B C35B C34B 117.9(4) . . ?
C30B C35B C34B 119.9(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1A H1 N1B 0.84 1.80 2.633(5) 170.2 2_757
O1B H27 N1A 0.84 1.98 2.789(5) 160.4 2_746

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.77
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.057

# start Validation Reply Form
_vrf_PUBL024_GLOBAL              
;
PROBLEM: The number of authors is greater than 5.
RESPONSE: J. Thun, J. Breu and W. Milius did all X-ray experiments, J. Thun and
B. Wedel did most of the lab work, A. Ridder and P. Moersdorf also worked in
their lab to crystallize the montelukast acid.
;
# end Validation Reply Form
loop_
_publcif_jmolscript.group
_publcif_jmolscript.id
_publcif_jmolscript.model
_publcif_jmolscript.model_type
_publcif_jmolscript.type
_publcif_jmolscript.type_group
_publcif_jmolscript.caption
_publcif_jmolscript.script

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