#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:46:15 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179595 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/59/4505957.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4505957
loop_
_publ_author_name
'Sanphui, Palash'
'Bolla, Geetha'
'Nangia, Ashwini'
_publ_section_title
;
 High Solubility Piperazine Salts of the Nonsteroidal Anti-Inflammatory
 Drug (NSAID) Meclofenamic Acid
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2023
_journal_paper_doi               10.1021/cg300002p
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C19 H15 Cl2 N2 O2'
_chemical_formula_weight         374.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.099(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4180(6)
_cell_length_b                   8.2144(6)
_cell_length_c                   28.770(2)
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1072
_cell_measurement_theta_min      2.7528
_cell_volume                     1739.6(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8621
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.9264
_exptl_absorpt_correction_T_min  0.8729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0892
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²+3.3964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1922
_refine_ls_wR_factor_ref         0.2088
_reflns_number_gt                1726
_reflns_number_total             2487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300002p_si_002.cif
_cod_data_source_block           MFA2-BPY
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4505957
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'
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
Cl1 Cl 0.1923(3) 0.5442(3) 0.25714(8) 0.1072(8) Uani 1 1 d .
Cl2 Cl 0.3715(3) 1.0736(3) 0.36134(8) 0.1106(8) Uani 1 1 d .
C2 C 0.1391(7) 0.5916(6) 0.40687(17) 0.0469(13) Uani 1 1 d .
N1 N 0.2851(7) 0.7218(7) 0.34532(17) 0.0640(15) Uani 1 1 d .
C5 C -0.1633(8) 0.7847(8) 0.3833(2) 0.0641(16) Uani 1 1 d .
H5 H -0.2657 0.8489 0.3751 0.077 Uiso 1 1 calc R
N2 N 0.4048(7) 0.7330(6) 0.01784(17) 0.0596(13) Uani 1 1 d .
C1 C 0.2997(8) 0.4869(7) 0.4202(2) 0.0554(15) Uani 1 1 d D
C17 C 0.0834(7) 0.5483(6) 0.00376(17) 0.0472(13) Uani 1 1 d .
C3 C -0.0091(8) 0.5814(7) 0.43115(19) 0.0586(15) Uani 1 1 d .
H3 H -0.0065 0.5078 0.4558 0.070 Uiso 1 1 calc R
O2 O 0.2873(6) 0.3964(5) 0.45741(14) 0.0730(13) Uani 1 1 d D
C7 C 0.1371(7) 0.7044(7) 0.36970(17) 0.0485(13) Uani 1 1 d .
O1 O 0.4325(6) 0.4851(6) 0.39937(15) 0.0810(14) Uani 1 1 d D
C18 C 0.2090(8) 0.5474(7) -0.02763(19) 0.0600(16) Uani 1 1 d .
H18 H 0.1883 0.4836 -0.0544 0.072 Uiso 1 1 calc R
C8 C 0.2830(7) 0.8189(8) 0.30495(19) 0.0583(16) Uani 1 1 d .
C13 C 0.2414(8) 0.7500(9) 0.2602(2) 0.0712(18) Uani 1 1 d .
C6 C -0.0176(7) 0.7990(7) 0.35857(18) 0.0574(15) Uani 1 1 d .
H6 H -0.0222 0.8731 0.3340 0.069 Uiso 1 1 calc R
C16 C 0.1246(9) 0.6455(7) 0.0424(2) 0.0671(17) Uani 1 1 d .
H16 H 0.0448 0.6525 0.0649 0.080 Uiso 1 1 calc R
C19 C 0.3648(9) 0.6394(8) -0.0200(2) 0.0655(17) Uani 1 1 d .
H19 H 0.4459 0.6363 -0.0422 0.079 Uiso 1 1 calc R
C4 C -0.1605(9) 0.6761(8) 0.4202(2) 0.0676(17) Uani 1 1 d .
H4 H -0.2591 0.6677 0.4371 0.081 Uiso 1 1 calc R
C15 C 0.2850(9) 0.7329(8) 0.0478(2) 0.0695(18) Uani 1 1 d .
H15 H 0.3099 0.7961 0.0747 0.083 Uiso 1 1 calc R
C12 C 0.2386(10) 0.8401(13) 0.2199(2) 0.086(2) Uani 1 1 d .
C11 C 0.2813(11) 1.0027(14) 0.2254(3) 0.105(3) Uani 1 1 d .
H11 H 0.2827 1.0659 0.1986 0.126 Uiso 1 1 calc R
C10 C 0.3214(10) 1.0754(10) 0.2676(3) 0.091(2) Uani 1 1 d .
H10 H 0.3484 1.1860 0.2696 0.109 Uiso 1 1 calc R
C9 C 0.3216(9) 0.9821(9) 0.3077(2) 0.0730(18) Uani 1 1 d .
C14 C 0.1831(14) 0.7718(15) 0.1727(3) 0.148(4) Uani 1 1 d .
H14A H 0.2674 0.6885 0.1663 0.223 Uiso 1 1 calc R
H14B H 0.1824 0.8566 0.1498 0.223 Uiso 1 1 calc R
H14C H 0.0636 0.7259 0.1715 0.223 Uiso 1 1 calc R
H2 H 0.404(5) 0.335(6) 0.4661(18) 0.13(3) Uiso 1 1 d D
H1 H 0.366(10) 0.648(10) 0.351(3) 0.11(3) Uiso 1 1 d .
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'
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_3
C3 C2 C7 119.3(5) .
C3 C2 C1 120.0(5) .
C7 C2 C1 120.7(5) .
C7 N1 C8 123.3(5) .
C7 N1 H1 115(5) .
C8 N1 H1 119(5) .
C6 C5 C4 121.0(6) .
C6 C5 H5 119.5 .
C4 C5 H5 119.5 .
C15 N2 C19 115.8(5) .
O1 C1 O2 122.5(5) .
O1 C1 C2 123.6(5) .
O2 C1 C2 113.9(5) .
C16 C17 C18 115.8(5) .
C16 C17 C17 122.3(6) 3_565
C18 C17 C17 121.9(6) 3_565
C4 C3 C2 122.1(5) .
C4 C3 H3 118.9 .
C2 C3 H3 118.9 .
C1 O2 H2 110(3) .
N1 C7 C6 120.7(5) .
N1 C7 C2 121.1(5) .
C6 C7 C2 118.2(5) .
C17 C18 C19 121.1(5) .
C17 C18 H18 119.4 .
C19 C18 H18 119.4 .
C9 C8 C13 117.8(6) .
C9 C8 N1 121.8(6) .
C13 C8 N1 120.4(6) .
C12 C13 C8 122.3(7) .
C12 C13 Cl1 120.1(6) .
C8 C13 Cl1 117.5(5) .
C5 C6 C7 121.0(5) .
C5 C6 H6 119.5 .
C7 C6 H6 119.5 .
C17 C16 C15 119.7(6) .
C17 C16 H16 120.1 .
C15 C16 H16 120.1 .
N2 C19 C18 122.9(6) .
N2 C19 H19 118.5 .
C18 C19 H19 118.5 .
C3 C4 C5 118.5(6) .
C3 C4 H4 120.8 .
C5 C4 H4 120.8 .
N2 C15 C16 124.7(5) .
N2 C15 H15 117.6 .
C16 C15 H15 117.6 .
C13 C12 C11 116.5(7) .
C13 C12 C14 122.9(10) .
C11 C12 C14 120.4(9) .
C10 C11 C12 123.6(7) .
C10 C11 H11 118.2 .
C12 C11 H11 118.2 .
C11 C10 C9 118.7(8) .
C11 C10 H10 120.6 .
C9 C10 H10 120.6 .
C8 C9 C10 121.0(7) .
C8 C9 Cl2 120.0(5) .
C10 C9 Cl2 119.0(6) .
C12 C14 H14A 109.5 .
C12 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C12 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C13 1.729(7) .
Cl2 C9 1.716(7) .
C2 C3 1.376(7) .
C2 C7 1.414(7) .
C2 C1 1.481(8) .
N1 C7 1.381(7) .
N1 C8 1.408(7) .
N1 H1 0.86(8) .
C5 C6 1.370(8) .
C5 C4 1.385(8) .
C5 H5 0.9300 .
N2 C15 1.313(7) .
N2 C19 1.337(7) .
C1 O1 1.215(7) .
C1 O2 1.315(6) .
C17 C16 1.372(7) .
C17 C18 1.375(7) .
C17 C17 1.464(10) 3_565
C3 C4 1.371(8) .
C3 H3 0.9300 .
O2 H2 1.01(2) .
C7 C6 1.390(7) .
C18 C19 1.375(8) .
C18 H18 0.9300 .
C8 C9 1.371(9) .
C8 C13 1.404(8) .
C13 C12 1.374(9) .
C6 H6 0.9300 .
C16 C15 1.382(8) .
C16 H16 0.9300 .
C19 H19 0.9300 .
C4 H4 0.9300 .
C15 H15 0.9300 .
C12 C11 1.377(12) .
C12 C14 1.480(11) .
C11 C10 1.353(12) .
C11 H11 0.9300 .
C10 C9 1.385(9) .
C10 H10 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
