#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/42/2004225.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_2004225
loop_
_publ_author_name
'Kokila, M. K.'
'Jain, A.'
Puttaraja
'Kulkarni, M. V.'
'Shivaprakash, N. C.'
_publ_section_title
;
 4-(4-Chloroanilinomethyl)-6-methylcoumarin
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2585
_journal_page_last               2586
_journal_paper_doi               10.1107/S0108270195006263
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C17 H14 Cl N O2'
_chemical_formula_weight         299.77
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source
'Cromer & Mann (1968) and Stewart, Davidson & Simpson (1965)'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.040(3)
_cell_length_b                   5.8040(10)
_cell_length_c                   17.728(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    300
_cell_measurement_theta_max      50
_cell_measurement_theta_min      40
_cell_volume                     1444.6(4)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7093
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2903
_diffrn_reflns_theta_max         24.9
_diffrn_standards_interval_count 167
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.26
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      1.37
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   4.41
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     246
_refine_ls_number_reflns         1300
_refine_ls_R_factor_obs          0.041
_refine_ls_shift/esd_max         0.623
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.033
_reflns_number_observed          2218
_reflns_number_total             2530
_reflns_observed_criterion       I>2.5\s(I)
_cod_data_source_file            cr1165.cif
_cod_data_source_block           cr1165a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1444.7(4)
_cod_database_code               2004225
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
Cl .88690(10) .0420(2) .39150(10) 5.71(5)
O(1) 1.13840(10) -0.2085(5) -.07100(10) 4.60(12)
O(2) 1.19580(10) .0775(5) -.00250(10) 6.01(14)
C(2) 1.1260(2) -.0289(7) -.0216(2) 4.32(17)
C(3) 1.0286(2) .0224(7) .0042(2) 4.04(17)
C(4) .9555(2) -0.1094(6) -.0185(2) 3.58(16)
C(5) .8984(2) -0.4435(7) -.0996(2) 4.03(16)
C(6) .9175(2) -0.6181(7) -0.1496(2) 4.32(17)
C(7) 1.0125(2) -0.6596(7) -0.1723(2) 4.83(19)
C(8) 1.0841(2) -0.5220(7) -0.1443(2) 4.69(18)
C(9) 1.0635(2) -0.3444(7) -.0954(2) 4.03(17)
C(10) .9698(2) -0.2978(6) -.0703(2) 3.52(16)
C(11) .8575(2) .1055(6) .1385(2) 3.57(16)
C(12) .9012(2) -.0879(6) .1710(2) 3.73(16)
C(13) .9106(2) -0.1054(6) .2487(2) 3.77(16)
C(14) .8766(2) .0668(7) .2936(2) 3.96(17)
C(15) .8342(2) .2613(7) .2633(2) 4.58(18)
C(16) .8252(2) .2800(7) .1856(2) 4.32(18)
N(1) .8466(2) .1300(6) .06140(10) 4.44(15)
C(17) .8543(2) -.0657(7) .0106(2) 4.33(17)
C(18) .8378(3) -0.7695(8) -0.1813(2) 5.5(2)
H(3) 1.022(2) .178(6) .0460(10) 6.1(9)
H(5) .824(2) -0.406(5) -.0820(10) 5.7(8)
H(7) 1.033(2) -0.795(7) -0.213(2) 8.8(11)
H(8) 1.154(2) -0.552(6) -0.1640(10) 6.9(9)
H(12) .925(2) -0.218(5) .1370(10) 4.3(7)
H(13) .939(2) -0.248(6) .274(2) 7.3(9)
H(15) .815(2) .388(6) .2980(10) 6.6(9)
H(16) .790(2) .415(6) .1630(10) 6.0(8)
H(N1) .804(3) .216(7) .048(2) 10.8(12)
H(17A) .831(2) -0.208(6) .0340(10) 5.4(8)
H(17B) .812(2) -.034(5) -.0370(10) 5.2(7)
H(18A) .823(2) -0.727(6) -0.2380(10) 6.9(9)
H(18B) .855(2) -0.935(6) -0.1780(10) 6.4(8)
H(18C) .777(2) -0.742(5) -0.1460(10) 5.6(8)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(9) O(1) C(2) 122.4(2) yes
O(1) C(2) O(2) 117.7(3) yes
O(1) C(2) C(3) 118.0(3) yes
O(2) C(2) C(3) 124.3(3) yes
C(2) C(3) C(4) 120.1(3) yes
C(3) C(4) C(10) 121.1(3) yes
C(3) C(4) C(17) 121.0(3) yes
C(10) C(4) C(17) 117.9(3) yes
C(4) C(10) C(9) 118.3(3) yes
C(4) C(10) C(5) 126.1(3) yes
C(5) C(10) C(9) 115.6(3) yes
C(10) C(9) O(1) 119.9(3) yes
C(8) C(9) O(1) 117.7(3) yes
C(10) C(9) C(8) 122.4(3) yes
C(9) C(8) C(7) 120.5(3) yes
C(8) C(7) C(6) 119.2(3) yes
C(7) C(6) C(5) 119.6(3) yes
C(18) C(6) C(5) 121.2(3) yes
C(6) C(5) C(10) 122.7(3) yes
C(4) C(17) N(1) 114.0(3) yes
C(17) N(1) C(11) 121.6(3) yes
N(1) C(11) C(12) 122.4(3) yes
N(1) C(11) C(16) 118.9(3) yes
C(16) C(11) C(12) 118.7(3) yes
C(11) C(12) C(13) 120.5(3) yes
C(12) C(13) C(14) 119.5(3) yes
C(13) C(14) C(15) 121.5(3) yes
C(14) C(15) C(16) 119.2(3) yes
C(15) C(16) C(11) 120.7(3) yes
C(13) C(14) Cl 119.3(3) yes
C(15) C(14) Cl 119.2(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.372(4) yes
O(2) C(2) 1.208(4) yes
C(2) C(3) 1.472(4) yes
C(3) C(4) 1.341(5) yes
C(4) C(10) 1.443(5) yes
C(10) C(9) 1.415(4) yes
C(9) O(1) 1.384(4) yes
C(9) C(8) 1.377(5) yes
C(8) C(7) 1.376(5) yes
C(7) C(6) 1.414(5) yes
C(6) C(18) 1.529(5) yes
C(6) C(5) 1.373(5) yes
C(5) C(10) 1.410(5) yes
C(4) C(17) 1.533(4) yes
C(17) N(1) 1.454(5) yes
N(1) C(11) 1.383(4) yes
C(11) C(12) 1.403(5) yes
C(12) C(13) 1.388(4) yes
C(13) C(14) 1.364(5) yes
C(14) C(15) 1.384(5) yes
C(15) C(16) 1.388(5) yes
C(16) C(11) 1.389(5) yes
C(14) Cl 1.748(3) yes
